Woodbury Homes under $600,000

Welcome to Woodbury, Connecticut—a picturesque town nestled in the heart of Litchfield County, where charming New England landscapes meet a vibrant community spirit. Known for its rich history and stunning natural beauty, Woodbury offers a serene escape from the hustle and bustle of city life, making it an ideal place for families, retirees, and anyone seeking a peaceful lifestyle.

Woodbury boasts a unique blend of rural charm and modern convenience. With its historic downtown area filled with quaint shops, delightful eateries, and local art galleries, residents can enjoy a small-town atmosphere while having access to essential amenities. The town is also home to beautiful parks, scenic trails, and recreational facilities, perfect for outdoor enthusiasts and nature lovers alike.

For those looking to plant their roots in this idyllic setting, Woodbury offers a variety of homes under $600,000. From charming colonial-style houses to cozy ranches, there’s something to suit every taste and lifestyle. These properties often come with spacious yards, providing ample space for gardening, play, or simply enjoying the tranquil surroundings.

With excellent schools, a strong sense of community, and a welcoming atmosphere, Woodbury is not just a place to live—it's a place to thrive. Whether you’re a first-time homebuyer or seeking a peaceful retreat, discover the charm of Woodbury and find your dream home today. Embrace the beauty of Connecticut living in a town that truly feels like home.

Newest Woodbury Homes under $600,000

$124,900

1 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24212678 MLS ⋅ Quassuk Heights Gardens BLDG.

Welcome to this delightful and exceptionally well cared for condo in the charming town of Woodbury! Just minutes from Main Street, this desirable first floor end unit offers plenty of light, a spacious bedroom, an open concept living/dining area, with wood floors throughout. There are great views of Litchfield County's rolling hills outside the front window and a tranquil shared patio in the back, abutting greenery and woodland. Why rent when you can own? HOA includes heat, hot water, trash, grounds maintenance, snow removal. No pets or smoking allowed.

22 Pilgrim Trl Unit G1, Woodbury

$529,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24210084 MLS

Looking for a convenient in town location? Built in 1940, this delightful vintage colonial is loaded with the charm of the 1940's. The front to back living room offers a fireplace, built ins as well as oak flooring. It also features a French door to the rear porch overlooking the spacious rear yard. Located adjacent to the kitchen, the formal dining room features a built-in china closet and oak flooring. A powder room and laundry area complete the main level. Upstairs, a front to back primary bedroom with oak flooring. There are two bedrooms and a full bath on this level. Need more room? The walk-up attic is floored provides the opportunity for future expansion. There is a rec room on the lower level for additional space.

11 Judson Ave, Woodbury

$290,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24210496 MLS ⋅ Woodbury Village BLDG.

Rare opportunity in desirable Woodbury Village! This charming three-level townhouse offers flexible living space, beautiful natural light, and a peaceful setting in the heart of Woodbury. The main level welcomes you with a spacious living room featuring a large bay window and abundant natural light. The adjoining eat-in kitchen offers generous pantry storage and sliders leading to a private deck overlooking a lovely wooded green space-the perfect spot for morning coffee or relaxing outdoors. A convenient half bath with laundry and additional storage completes this level. Upstairs, you'll find two generously sized bedrooms with ample closet space, including a walk-in closet, along with a full bath and additional linen storage. The finished walk-out lower level adds valuable bonus space and offers endless possibilities as a home office, recreation room, guest space, gym, or additional living area. Sliding doors open to a covered outdoor area and backyard space. The basement has also been waterproofed and features newer carpeting. Additional features include space for a private garden, three portable air-conditioning units (one with heat), a basement dehumidifier, and deck furniture included by the seller. Woodbury Village offers a tranquil setting with expansive green space, mature trees, walking areas, and a river running through the complex-all while being conveniently located just minutes from Woodbury's shops, restaurants, and everyday amenities.

74 Washington Road Unit 40, Woodbury

$199,900

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24209657 MLS ⋅ Town In Country BLDG.

Welcome to 229 Bacon Pond Rd Unit 312 - located in the Town In Country complex, this 2 bed/1 bath unit has been remodeled from top to bottom featuring a brand new kitchen, new flooring, and central air. Inside you'll find an open floor plan perfect for entertaining - the kitchen has been completely redesigned featuring new cabinets, quartz countertops, and stainless steel appliances. The modern flooring flows from the kitchen to the fireplace, offering a perfect place for family gatherings. Around the corner you'll find two bedrooms and 1 full bath - the bathroom has been updated and modernized featuring a brand new vanity and tiled shower. The slider door leads to a private patio which is just a short walk down to the in ground pool. Enjoy everything Woodbury has to offer - Rt. 6 is minutes away offering plenty of restaurants and shopping, with I84 just a short drive away. Whether you enjoy laying by the pool or hiking through a number of trails this is the perfect location for the discerning consumer.

229 Bacon Pond Rd Unit 312, Woodbury

$294,900

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24209304 MLS ⋅ Woodlake BLDG.

Welcome to 47 Woods Way! This beautifully renovated Woodlake townhouse is truly move-in ready, offering stylish updates and the convenience of a garage just steps from your front door. Step inside to discover a gorgeous new kitchen featuring crisp white Shaker cabinetry, gleaming quartz countertops, and stainless steel appliances. New RevWood by Mohawk flooring flows throughout the first floor, complemented by a charming shiplap-accented fireplace that creates a warm and inviting focal point in the living room. Upstairs, the spacious primary suite offers a beautifully renovated ensuite bathroom, creating a private retreat at the end of the day. Enjoy a brand-new tiled shower with niche, modern vanity and tasteful finishes. The guest bathroom has also been thoughtfully updated with new porcelain tile flooring, oak vanity, new lighting, and mirror. Plush new wall-to-wall carpeting throughout the second floor lends a cozy, fresh feel to the bedrooms. A brand new hot water heater, and a two year old HVAC system add comfort and peace of mind. The amenities continue with a garage featuring a new door opener, plus a full unfinished basement offering excellent storage and flexibility. A newer washer and dryer and a private sun deck off the living room round out the package. With its fresh renovations, thoughtful updates, and convenient location, 47 Woods Way offers the perfect blend of style, comfort, and easy living. Just unpack and enjoy!

47 Woods Way Unit 47, Woodbury

$550,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24206868 MLS

Charming Brick Ranch on 2+ Acres Nestled on more than two acres in a peaceful setting, this well-built brick ranch offers the perfect blend of privacy, comfort, and convenience, with easy access to shopping, dining, and everyday amenities. The home has been freshly painted, meticulously maintained, and reflects pride of ownership throughout. Inside, you'll find a spacious and inviting floor plan featuring hardwood flooring in the living room and all three bedrooms, adding warmth and character to the main living spaces. The kitchen and pantry are finished with durable vinyl flooring, providing easy care and everyday practicality. The generously sized kitchen features ample counter space, a pantry, a cozy eating area, and a gas fireplace, making it an ideal gathering place for family and friends. The living room is enhanced by built-in bookcases, while the bedrooms offer hardwood floors and built-in desks, combining charm with functionality. The primary bedroom includes a private full bath, creating a comfortable retreat. Additional highlights include a lower-level room, a workshop with walkout access, a tandem garage with room for vehicles and storage, and a fully insulated walk-up attic offering exciting possibilities for future expansion, hobbies, or additional storage. If you're looking for a solidly constructed home with acreage, character, and room to grow, this property presents a rare opportunity to enjoy country-style tranquility without sacrificing convenien

578 Old Sherman Hill Rd, Woodbury

$274,900

2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24206920 MLS ⋅ Woodlake BLDG.

Welcome home to Woodlake! The Woodlake community provides non-motorized boating on the lake, hiking trails, basketball, tennis courts, and a playground area for the kids to name a few. This end unit is within a short walking distance of the lake, clubhouse and other complex amenities! Spacious and bright, this Congeniality II model offers an open floor plan, and two spacious bedrooms with 2.5 baths. Freshly painted, this unit's kitchen offers newer cabinets, appliances and fixtures. The expansive combination living and dining room features hardwood floors and ample space to host the upcoming holidays! Off the living room, step out onto the back deck to grill and enjoy seasonal views of the lake. The main level is finished off by an updated half bath. The upper level offers two generously sized bedrooms, including two full bathrooms. The primary-suite features laminate flooring, plenty of closet space, and stall shower. The second level full bath has newer vanity, granite countertops and custom built-in. Newer carpet lines the stairs down to the mostly finished basement. This space provides another option for livable space, or additional room for play or work including a private patio. Both sliders have been recently replaced. This well-maintained community provides a responsive, on-site property management company. Live in Woodbury for under 300k with no exterior maintenance demands! Woodlake is in close proximity of Woodbury and Southbury town centers!

3 Shagbark Ln Unit 3, Woodbury

$289,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24205782 MLS ⋅ Woodlake BLDG.

Woodlake has 7 Ranch Style Units with either a carport or garage; making #5 Alder Court is a rare-find-end unit! The walk from the parking area is level to an inviting Court-yard and onto this lovely ranch style home. You will notice the natural private surroundings. Once inside, beautiful wood floors greet you. Beautiful windows provide natural sunlight. The LR has a cathedral ceiling. The Fireplace, (one of two) has been sealed shut for safety. Woodlake will allow wood-burning or pellet stove inserts with permits. The Woodlake Office can assist with the paperwork. The galley kitchen has new granite tops. The Primary Bedroom is ensuite. There is ample storage and closets in both bedrooms. The Walk-out Lower Level is finished with newer vinyl flooring. There is a laundry room with set-sink. Included are two working washing machines, (The small washer was used for baby clothes) a dryer and set-sink.the ping-pong table can be yours if you wish! The quintessential Town of Woodbury was recently voted The Best small Town in CT by Readers Digest and the Boston Globe. It's an easy commute east or west to I84. There are two Town Greens, and restaurants to delight every palate. There are parks to enjoy, trails to hike, garden, performing arts and learning centers. Explore Boutiques, Antiques and visit the Woodbury portion of the CT Wine Trail! This is a beautiful time of Year at Woodlake and in Woodbury CT! Visit soon!

5 Alder Ct Unit 84A, Woodbury

$599,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24207451 MLS

The John Cramer House at 10 Weekeepeemee Road is listed on the National Register of Historic Places and is a wonderful example of Greek Revival architecture. Rich in period character, the home features beautiful chestnut plank flooring, nearly 9-foot ceilings, and an original fireplace with a beehive oven. The first floor offers a study, living room, dining room, granite-countered kitchen, and a charming breakfast room with wood stove and half bath. Upstairs are three bedrooms, a full bath with marble counter, and conveniently located laundry. A full walk-up attic leads to a large finished space with additional storage and closet space. An attached shed provides a potting area and stairs to a second-floor loft. Set on 3.09 acres, the property also includes a historic barn with a two-car garage, two horse stalls, and a full second floor. Open field and wooded areas create a peaceful country setting, with elevated views toward the town of Woodbury from the upper portion of the property. Across the road, enjoy seasonal views of the Weekeepeemee River, adding to the charm and character of this special historic property.

10 Weekeepeemee Rd, Woodbury

$209,900

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24206004 MLS ⋅ Town In Country BLDG.

Move right into this beautifully renovated upper end unit in Woodbury's desirable in-town Town & Country condominium complex. Tastefully updated throughout, this light-filled unit features an open floor plan with a completely renovated kitchen flowing into the living room with fireplace and built-ins. Updates include new windows, luxury vinyl plank flooring, interior doors, lighting, switches, outlets, and electrical finishes throughout. Ideally located toward the rear of the complex, the unit overlooks the pool and landscaped grounds, offering a peaceful setting with added privacy. One of the standout units in the complex, this turnkey property combines quality updates, an excellent location, and the convenience of being within walking distance to shops, restaurants, and everything historic Woodbury has to offer.

229 Bacon Pond Rd Unit 313, Woodbury

$420,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24203216 MLS

Welcome to 34 Pilgrim Trail, a home thoughtfully cared for and enjoyed for 25.5 years. This peaceful Woodbury property features granite kitchen countertops, a tiled backsplash, stainless-steel appliances, and a ceramic kitchen floor. Solid pine doors throughout the home add warmth and character. The upstairs bathroom has been beautifully updated, including the tub and a solid-rock vanity countertop. The upper bedroom/closet offers flexible use and can easily be converted back to a bedroom. Additional improvements include updated closet systems, a refreshed closet near the upstairs bathroom, and a roof installed in 2011. The home is generator-ready, with the generator located outside. Enjoy the tranquility of the property while remaining just minutes from Main Street, shopping, and New Morning Market. Nearby schools and everyday conveniences make this a wonderful place to call home.

34 Pilgrim Trl, Woodbury

$299,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24200604 MLS ⋅ Condos At Woodlake BLDG.

PRETTY AND SO PRIVATE!! Enjoy nature right from your back door in this spacious, freshly painted 3-bedroom home! Imagine relaxing with a cup of coffee on your private deck. Kitchen is nicely updated with large pantry, stainless appliances, dining area and ceiling fan. The living room features a warming fireplace with Pellet Stove for an economical heat source. and the dining room boasts sliders that open to the rear deck. Upstairs, you'll find three comfortable bedrooms and two full baths, plus there's an extra room in the finished lower level, perfect for office, media room or workout room. You'll love all the amenities Woodlake has to offer, like walking trails, a pond for canoeing, picnic areas, and a playground. The town of Woodbury itself is fantastic, with a wine trail, excellent restaurants, and charming antique shops to explore. Plus, it's super convenient to the highway, shops, and schools. Woodlake is such a wonderful community.

8 Woods Way Unit 8, Woodbury

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Woodbury Homes under $600,000

Newest Woodbury Homes under $600,000

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