Recently Sold Woodbury Homes

• 

  $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
• 

  $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
• 

  $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
• 

  $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
• 

  $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
• 

  $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
• 

  $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
• 

  $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
• 

  $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
• 

  $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
• 

  $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
• 

  $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
• 

  $515,000 Sold Jun 30, 2025

  • 1,918 Sq Ft
  • $269/SF
  • 44 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1820

  7 Orenaug Ave, Woodbury, CT 06798

  New to market.....Lovely, classic antique colonial just off Main Street in center of town Woodbury. Home has been updated, expanded and well maintained over the years. Spacious family room off kitchen and primary bedroom/bath reflect today's lifestyle. Beautiful and private backyard. Easy walk to everything Woodbury offers.

  Lisa Titcomb William Pitt Sotheby's Int'l

  7 Orenaug Ave, Woodbury, CT 06798
• 

  $897,000 Sold Jun 27, 2025

  • 2,894 Sq Ft
  • $310/SF
  • 27 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2015

  332 Good Hill Rd, Woodbury, CT 06798

  Stunning reproduction of a mid-1700s New England Center-Chimney Cape, masterfully built in 2015 and set on 3.3+/- acres. This 3-bed, 3-bath home blends timeless craftsmanship-12-over-12 windows, wide plank circle-sawn floors, custom trim and paneling-with modern luxuries including smart home tech, soapstone counters, and a showpiece kitchen hearth. Enjoy nearly 2,900 sq ft of living space,

  Rebecca Doh W. Raveis Lifestyles Realty

  332 Good Hill Rd, Woodbury, CT 06798
• 

  $499,000 Sold Jun 16, 2025

  • 1,648 Sq Ft
  • $303/SF
  • 3 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1972

  98 Old Town Farm Rd, Woodbury, CT 06798

  Discover this inviting ranch style, one level living home featuring three bedrooms and two and a half baths, beautifully situated on a scenic lot. A separate front entrance leads into a convenient mudroom that also serves as the laundry area and access to the garage.The spacious living and dining room boasts a charming brick fireplace with a wood stove, perfect for cozy gatherings. The remodeled

  Jeff Boucher Drakeley Real Estate, Inc.

  98 Old Town Farm Rd, Woodbury, CT 06798
• 

  $290,000 Sold Jun 13, 2025

  • 1,773 Sq Ft
  • $164/SF
  • 16 Days On Market

  • 2 Beds
  • 3 Baths
  • Built 1980

  1 Woods Way Unit 118E, Woodbury, CT 06798

  Country Living at its finest in award winning Woodbury CT. Recently voted The Best Small Town in CT by The Boston Globe and Readers Digest! This home has been remodeled and is in immaculate Move-in-Ready condition. The Fireplace has a pellet stove for cozy winter warmth. The Living room/dining area offer inviting wood toned floors. The deck is accessed via the LR slider. There is a lovely stretch

  Terry Lee Adams Adams & Adams Real Estate

  1 Woods Way Unit 118E, Woodbury, CT 06798
• 

  $1,050,000 Sold Jun 06, 2025

  • 3,928 Sq Ft
  • $267/SF
  • 34 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2008

  17 Transylvania Rd, Woodbury, CT 06798

  A stunning 4-bedroom, 2.5-bathroom colonial nestled on a private 2-acre lot, set back along a winding newly decorative stone driveway in an estate-like setting. This beautifully designed home boasts an open floor plan with high ceilings-9+ feet in most rooms and soaring to 10.5 feet in the living room-refined finishes, and luxurious upgrades throughout. The gourmet kitchen features granite

  Michael Hvizdo Coldwell Banker Realty

  17 Transylvania Rd, Woodbury, CT 06798
• 

  $415,000 Sold Jun 04, 2025

  • 1,796 Sq Ft
  • $231/SF
  • 55 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1985

  23 Woodbury Hill, Woodbury, CT 06798

  Perhaps the most desirable condominium complex in Woodbury, Woodbury Hill offers a quiet, beautiful, rural location, yet is close to shopping and accessible to major routes. This Putnam's Loft offers a spacious, open entertaining area with living room open to dining room with oak flooring, fireplace and lots of light. The updated kitchen provides access to the deck overlooking rear property. With

  Donna Bannon BHGRE Bannon & Hebert

  23 Woodbury Hill, Woodbury, CT 06798
• 

  $184,000 Sold May 28, 2025

  • 913 Sq Ft
  • $202/SF
  • 56 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1971

  229 Bacon Pond Rd Unit 132, Woodbury, CT 06798

  Ready for immediate occupancy in Woodbury's Town in Country community is this freshly painted two bedroom, one bath condominium with new laminate floors throughout, a new oven/range, microwave and dishwasher. Sliders in the living room lead to a patio with a sun-lit, open view. A great opportunity to live in one of Connecticut's favorite towns.

  Tom Greto William Raveis Real Estate

  229 Bacon Pond Rd Unit 132, Woodbury, CT 06798
• 

  $280,000 Sold May 28, 2025

  • 1,482 Sq Ft
  • $189/SF
  • 69 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1980

  22 Woods Way Unit 22, Woodbury, CT 06798

  Beautiful townhouses in the wonderful Woodlake complex. This unit is wonderfully updated and impeccably maintained. The well appointed kitchen is light & bright with corian countertops & stainless appliances. The living room is warm & inviting featuring cozy pellet stove, accent beams and slider to a private deck. Laundry & a lovely half bath on the main floor as well. Upstairs there are two good

  Joan Junga CB Country to Coast Realty

  22 Woods Way Unit 22, Woodbury, CT 06798
• 

  $875,000 Sold May 22, 2025

  • 3,978 Sq Ft
  • $220/SF
  • 149 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 2004

  447 Transylvania Rd, Woodbury, CT 06798

  Nestled at the intersection of Route 72 and Route 167 in Woodbury, this exceptional home is the perfect blend of modern amenities and unparalleled convenience. Located in close proximity to both the Center of Woodbury and the Southbury Green you'll be moments away from a diverse selection of shops and restaurants. Enjoy the close by natural beauty of Wood Lake, local parks, walking trails, and

  Casey French Litchfield County Real Estate

  447 Transylvania Rd, Woodbury, CT 06798
• 

  $1,720,000 Sold May 21, 2025

  • 9,296 Sq Ft
  • $185/SF
  • 31 Days On Market

  • 6 Beds
  • 7 Baths
  • Built 2006

  59 Hillside Rd, Woodbury, CT 06798

  Auction Opportunity. Please review FAQ and Property Information Package included in the additional documents on MLS (you may have to request these directly from your agent or the auction company). Asking Price is Opening Bid only. Final price will be determined by competitive bidding. All bidding online, opening April 23 at 4pm and ending April 30 at 4pm. Bidding website available upon request. ~

  Samantha Kelley Tranzon Auction Properties

  59 Hillside Rd, Woodbury, CT 06798
• 

  $160,000 Sold May 20, 2025

  • 913 Sq Ft
  • $175/SF
  • 36 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1971

  229 Bacon Pond Rd Unit 411, Woodbury, CT 06798

  Town In Country lower end unit in a great location within the complex. This unit features new mechanicals and appliances with 2 bedrooms, full bath and fireplace. Bright and sunny living space with a private patio out back overlooking the woods and rear yard. Convenient location to the pool and laundry, minutes from town, shopping and restaurants. Don't miss out.

  Jeff Boucher Drakeley Real Estate, Inc.

  229 Bacon Pond Rd Unit 411, Woodbury, CT 06798
• 

  $120,000 Sold May 19, 2025

  • 546 Sq Ft
  • $220/SF
  • 18 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1965

  16 Pilgrim Trail Unit 3, Woodbury, CT 06798

  First floor 1 bedroom unit in very good condition. Newer cabinets with granite countertops and hardwood floors. Heat, hot water, trash, snow removal, and grounds maintenance included. Occupied by long term tenant on month to month lease.

  Carlo Bettini Weichert REALTORS Briotti Group

  16 Pilgrim Trail Unit 3, Woodbury, CT 06798
• 

  $295,000 Sold May 15, 2025

  • 1,025 Sq Ft
  • $288/SF
  • 29 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1979

  3 Woodbury Place Unit 3, Woodbury, CT 06798

  Rare opportunity to own a Woodbury Place condo! Quaint community just minutes from all major conveniences, local restaurants, area schools, and major highway I-84. This end unit features wood burning stove to offset heating costs, and higher efficiency heat pump. The first floor includes dining area with slider to stone patio and galley kitchen offering quartz countertops, built-in pantry, and

  Katherine Parlato Drakeley Real Estate, Inc.

  3 Woodbury Place Unit 3, Woodbury, CT 06798
• 

  $456,000 Sold May 15, 2025

  • 1,550 Sq Ft
  • $294/SF
  • 62 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1895

  50 Washington Rd, Woodbury, CT 06798

  Step back in time with this beautiful Colonial-style home, full of character and charm, nestled in the heart of Woodbury. Built in 1895, this 3-bedroom, 1.5 bathroom property boasts classic colonial architecture with modern updates that make it both timeless and functional. The home features original hardwood floors and large windows that invite plenty of natural light. This spacious living room

  Rhya Szymansky Drakeley Real Estate, Inc.

  50 Washington Rd, Woodbury, CT 06798
• 

  $629,000 Sold May 13, 2025

  • 4,800 Sq Ft
  • $131/SF
  • 166 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1870

  514 Main St N, Woodbury, CT 06798

  Your home is your castle! If you've ever dreamed of calling a castle your home, this remarkable 5,000-square-foot stone house is the answer. Known fondly by locals as "The Castle," this property has a fascinating history, with roots tracing back to the 1800s but the all updates including new mechanicals, plumbing, electric, floors, well, septic, roof and more will give you comfort and peace of

  Pam Famiglietti William Raveis Real Estate

  514 Main St N, Woodbury, CT 06798
• 

  $290,000 Sold May 09, 2025

  • 1,456 Sq Ft
  • $199/SF
  • 4 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1979

  44 Woods Way Unit 44, Woodbury, CT 06798

  This spacious and sunny end-unit townhouse offers the perfect blend of comfort, convenience, and lifestyle-ideal for first-time buyers in sought after Woodlake community. With 2 bedrooms and 2 Full baths, this home features 1,456 sq ft of living space, plus an additional 855 sq ft of unfinished basement-perfect for hobbyists, a home gym, or extra storage. The updated kitchen includes stainless

  Kristie Perry William Pitt Sotheby's Int'l

  44 Woods Way Unit 44, Woodbury, CT 06798
• 

  $175,000 Sold May 02, 2025

  • 913 Sq Ft
  • $192/SF
  • 43 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1971

  229 Bacon Pond Rd Unit 214, Woodbury, CT 06798

  Town In Country is a lovely complex situated in the picturesque town of Woodbury, set back from the road yet close to the center of town, restaurants and shopping. This spacious condo offers 2 bedrooms, 1 full bath with a walk-in tub and a large open living/dining room area. Snuggle up in front of the fireplace during those cold winter months. Enjoy your morning coffee while lounging on your

  Cindy Sevell Coldwell Banker Realty

  229 Bacon Pond Rd Unit 214, Woodbury, CT 06798
• 

  $840,000 Sold May 02, 2025

  • 3,124 Sq Ft
  • $269/SF
  • 84 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 2019

  11 Saxony Ln, Woodbury, CT 06798

  Do not miss this beautiful home set back on a private 4.15-acre lot. Main level features a total open floor plan with vaulted ceilings and half bath. Kitchen features Kucht stainless steel appliances, Quartz countertops, with an oversized walk-in pantry. Extra Large dining, kitchen, family room area with built in sound system perfect for entertaining. Upper level adds 2 large bedrooms along with

  Chris Carey Carey & Guarrera Real Estate

  11 Saxony Ln, Woodbury, CT 06798
• 

  $850,000 Sold May 01, 2025

  • 1,628 Sq Ft
  • $522/SF
  • 260 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1850

  258 Washington Rd, Woodbury, CT 06798

  This recently fully renovated Antique has a combination of historic charm & modern amenities, which creates a truly exceptional living space. The potential for a pool adds an extra touch of luxury, while the delightful & well-maintained two-story barn in ready condition, presents exciting opportunities for conversion, whether for a guest house, pool house, or a private office on the 2nd floor

  Pat Lahoud William Pitt Sotheby's Int'l

  258 Washington Rd, Woodbury, CT 06798
• 

  $297,500 Sold Apr 30, 2025

  • 1,508 Sq Ft
  • $197/SF
  • 10 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1960

  51 Joshua Hill Rd, Woodbury, CT 06798

  Endless Potential in Woodbury! Discover the opportunity to own a single-family home in the charming town of Woodbury at an exceptional value. This three-bedroom, one-and-a-half-bathroom ranch is conveniently located near I-84 and Route 6, offering easy access to shopping, dining, and local amenities. While the home could benefit from some updates and TLC, it's a fantastic chance to bring your

  Sarah Perrotti Regency Real Estate, LLC

  51 Joshua Hill Rd, Woodbury, CT 06798
• 

  $895,000 Sold Apr 29, 2025

  • 2,600 Sq Ft
  • $344/SF
  • 31 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2021

  35 Fawn Meadow Ln, Woodbury, CT 06798

  Located in the heart of Woodbury, the antiques capital of Connecticut, with convenient access to the charming towns of Litchfield, Washington, and Roxbury, this newly built modern farmhouse offers a perfect balance of comfort and elegance. Thoughtfully designed with quality craftsmanship and energy-efficient features, this inviting retreat boasts 3 spacious bedrooms, 3.5 bathrooms, and a

  GREGORY COHEN William Pitt Sotheby's Int'l

  35 Fawn Meadow Ln, Woodbury, CT 06798
• 

  $628,500 Sold Apr 28, 2025

  • 1,008 Sq Ft
  • $624/SF
  • 228 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1987

  49 Jacks Bridge Rd, Woodbury, CT 06798

  Incredible opportunity at an affordable price! Discover the perfect blend of residential comfort and professional-grade amenities in this exceptional property located in the charming town of Woodbury, nestled in the scenic Litchfield County. This unique offering is ideal for car enthusiasts, hobbyists, or entrepreneurs seeking a versatile space that can serve as both a tranquil home and an

  Christine Green Ardor Real Estate

  49 Jacks Bridge Rd, Woodbury, CT 06798
• 

  $330,000 Sold Apr 23, 2025

  • 1,640 Sq Ft
  • $201/SF
  • 21 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1980

  42 Woods Way Unit 126F, Woodbury, CT 06798

  Woodlake in Woodbury an easy place to live in a great community. This three bedroom two full and one-half bath was built in 1980 and is ready for a new homeowner. End unit with plenty of light and a beautiful deck. The flooring is a combination of tile and carpet, and the floor plan is open and airy. The kitchen is a great size for a little coffee table, stainless appliances, white cabinets and

  Bonnie Wilson Berkshire Hathaway NE Prop.

  42 Woods Way Unit 126F, Woodbury, CT 06798
• 

  $952,000 Sold Apr 15, 2025

  • 5,915 Sq Ft
  • $161/SF
  • 132 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1997

  5 Bear Run, Woodbury, CT 06798

  Tucked away on a sought-after cul-de-sac, this open-layout home is crafted for exceptional entertaining. The light-filled, two-story foyer is framed by two sets of French doors: one opening to an office & the other leading to a living room that flows seamlessly into the dining room-an ideal setup for holiday gatherings. The custom kitchen, equipped with granite countertops, a center island, gas

  Shelley Drakeley Drakeley Real Estate, Inc.

  5 Bear Run, Woodbury, CT 06798
• 

  $735,000 Sold Apr 14, 2025

  • 2,042 Sq Ft
  • $360/SF
  • 45 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2022

  29 Fawn Meadow Ln, Woodbury, CT 06798

  Nestled in the heart of Woodbury, with easy access to the picturesque towns of Litchfield, Washington, and Roxbury, this newly constructed modern farmhouse-style home offers the perfect blend of comfort, privacy, and New England charm. Built with quality craftsmanship and energy-efficient features, this serene retreat boasts 3 spacious bedrooms, 2.5 bathrooms, plus a versatile 300+/- sq. ft.

  GREGORY COHEN William Pitt Sotheby's Int'l

  29 Fawn Meadow Ln, Woodbury, CT 06798
• 

  $291,000 Sold Apr 11, 2025

  • 1,300 Sq Ft
  • $224/SF
  • 22 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1974

  17 Tamarack Ln Unit 17, Woodbury, CT 06798

  Beautifully updated and cared for Ranch style end unit condo located at the end of Tamarack Lane overlooking a peaceful wooded landscape. Open floor plan with dining area and a vaulted family room that features a newer wood stove fireplace insert with gorgeous custom mantle with sliders to an updated Trex deck. Ceramic tile and hardwood floors grace the main level of this freshly painted home.

  Sharisse Steiner William Raveis Real Estate

  17 Tamarack Ln Unit 17, Woodbury, CT 06798
• 

  $925,000 Sold Apr 11, 2025

  • 3,786 Sq Ft
  • $244/SF
  • 4 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2008

  102 Quanopaug Trail, Woodbury, CT 06798

  Stunning! Dramatically open, spacious, modern colonial offers a perfect balance of comfort and elegance. Thoughtfully designed with quality craftsmanship and energy-efficient features, this inviting retreat boasts 4 spacious bedrooms, 3.5 bathrooms, and a generously sized finished "Wow" room with its own additional bedroom providing endless possibilities for a guest suite, home office, media room

  Nan Jane Keough William Pitt Sotheby's Int'l

  102 Quanopaug Trail, Woodbury, CT 06798
• 

  $590,000 Sold Apr 07, 2025

  • 2,628 Sq Ft
  • $225/SF
  • 8 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1930

  301 Transylvania Rd, Woodbury, CT 06798

  This unique 1930s Colonial home blends vintage charm with modern upgrades, offering endless possibilities. The main floor features a bright primary bedroom with French doors, a chef's kitchen with dual gas ovens and a Subzero refrigerator, two full baths, and two separate laundry areas for added convenience. The private apartment, with its own kitchen, deck, and entrances, is perfect for guests

  Jane Spino Showcase Realty, Inc.

  301 Transylvania Rd, Woodbury, CT 06798

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