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$483,000
3 Beds 2 Baths 24096286 MLS
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 updated kitchen, complete with granite countertops and a generous pantry. The open-concept layout seamlessly connects the eat-in kitchen to the living room, creating a warm and inviting space-perfect for everyday living and entertaining. The main level also includes a flexible room ideal for a home office or a potential first-floor bedroom to suit your lifestyle. Upstairs, you'll find three spacious bedrooms, a media room, and a tastefully finished full bath with convenient laundry hookups. The primary bedroom is a true retreat, featuring vaulted ceilings and French doors that open to a private balcony-perfect for morning coffee or evening relaxation. Set on nearly 2 acres of flat, usable land, this property offers a peaceful setting with ample space for outdoor living, gardening, and recreation. With easy access to nearby towns and local amenities, this home combines tranquility, style, and convenience-one you won't want to miss!

3 Lynns Corner Rd, Woodbury

$480,000
3 Beds 2 Baths 24125848 MLS
Charming one-level living in a beautiful setting. Enjoy the ease of one-level living in this thoughtfully designed home, nestled in a peaceful and scenic location. Step inside to an inviting open floor plan that seamlessly connects the bright living and dining areas-perfect for both relaxing and entertaining. Just off the dining room, you'll find a cozy family room ideal for gatherings or quiet evenings. The primary bedroom features a private half bath and a walk-in closet, offering comfort and convenience. Hardwood floors flow throughout all bedrooms as well as the main living and dining spaces, adding warmth and timeless style. Don't miss the opportunity to make this lovely home-- with newer roof and gutters-- yours!

145 Cat Swamp Rd, Woodbury

$480,000
5 Beds 4 Baths 24008400 MLS
A rare find in Woodbury; a sprawling 5-bedroom home accompanied by a legal in-law apartment, designed for harmonious multi-generational living. Nestled at the end of a quiet dead-end road, this raised ranch is set upon a wooded 4-acre lot, offering picturesque seasonal views of a Reichenback Pond. The heart of the home boasts an inviting open floor plan, highlighted by a maple wood kitchen with an expansive center island that seamlessly connects to the spacious living and dining areas. With three bedrooms and two full baths, comfort is paramount. Meanwhile, the legal in-law apartment, with its separate ground-level entrance, provides a private sanctuary complete with its own kitchen, living space, and two cozy bedrooms. Each dwelling enjoys its own outdoor deck/patio, while sharing the convenience of a common laundry area. Ideally positioned within a mere 5-minute drive from four town centers and a quick 10-minute jaunt to major routes. This property promises exceptional value but also an abundance of living space tailored to modern family needs.

171 Kimberly Ln, Woodbury

$477,000
3 Beds 3 Baths 24174440 MLS
Welcome to 38 Mountain Road, a perfect blend of functional living space and privacy while still offering a close proximity to town. Upon entering you are greeted with a warm and welcoming living room. This space flows into the dining room which is right next to the remodeled kitchen making dinner hosting a breeze! The kitchen offers a view of your private back yard from the window and beautiful granite and tile. Easily transition from in home cooking to grilling outside with the backyard just a step away. The first floor is completed with a family room featuring a slider door leading out to your brand new patio. This family room enjoys the same private view as the kitchen and includes a cozy fireplace. A half bath with laundry, an over sized closet for storage and access to your two car garage completes this level. Upstairs you will find a generous sized primary bedroom with a walk in closet and private full bathroom. Two more bedrooms offering ample space and another full bath complete this level. Hardwood floors, beautiful trim work, and an abundance of natural light are just a few features that you may enjoy. Home was reinsulated in 2023 making it more energy efficient.

38 Mountain Rd, Woodbury

$475,000
3 Beds 2 Baths 24050653 MLS
Nestled in the foothills of Litchfield County, in the town just voted "Cutest Town in Connecticut" and the antiquing capital of the northeast, 3 Lynns Corner Rd is a 2,400 sf, fully remodeled colonial, with a mix of both a southern French Quarter charm and a modern contemporary flair. Situated on 1.95 level acres with a berm of wildflowers and grape vines on the left and a river on the right, this property provides both privacy and convenience, located only 3 miles from downtown Woodbury antiquing and 3 miles from downtown Watertown shopping. The first floor boasts a fully remodeled kitchen, with brand new stainless appliances, a dining room, living room with built-in wine and beverage bar, office and full bathroom. The second floor has 3 bedrooms, a media room and a full bath all under a customized 17 foot tall, vaulted ceiling. All of the electrical and plumbing have been upgraded, with new light switches, fixtures, ceiling fans, recessed lights and electrical outlets, along with all new bathroom fixtures and custom tiling and all new luxury vinyl plank flooring. All the utilities (HVAC, water and filtration system) were replaced within the past 3 years. Both floors have separate heating and AC systems to help regulate the different environments. Whether sitting out on the front covered veranda with a cup of coffee or creating a bonfire in the backyard fire pit, this house is a special destination property. With room for a garage and a pool, the possibilities are endless.

3 Lynns Corner Rd, Woodbury

$475,000
4 Beds 2 Baths 170612934 MLS
Welcome to this beautiful Cape with over four acres of land nestled in the heart of Woodbury very private yet convenient to all shopping, parks, hiking trails, and antique shops. This home offers a serene and timeless escape. Main level has good size living room with woodburning fireplace. Kitchen has been updated with stainless steel appliances and granite counter tops. Gorgeous sunroom off the kitchen. There is a bedroom on main level and a full bath Mud room/laundry room complete main level. All hardwood flooring throughout the house. Second story has two good size bedrooms also has an office that can be a child's bedroom and one full bath. Plenty of build ins and closet space throughout this home. Partially finished Basement offers plenty of storage space with a woodburning stove. Newer full house generator. There are two attached garages, and two oversize detached garages/bay storage. Woodbury has been named "Most charming small town" by Readers Digest. Come and enjoy all award-winning restaurants and everything that Woodbury has to offer. Close to train stations 90 minutes to NYC.

27 Tuttle Rd, Woodbury

$473,100
3 Beds 2 Baths 24005975 MLS
Welcome to this lovingly cared for Cape-style home! This well maintained home boasts modern comforts, providing the perfect backdrop for a relaxed lifestyle. As you step inside, you're greeted by gleaming hardwood floors that flow seamlessly throughout the main level. The cozy ambiance is enhanced by not one, but two inviting fireplaces, where gatherings with loved ones are sure to create lasting memories. The sunroom offers a tranquil oasis, while the dining room provides an space for formal meals. The remodeled kitchen is a chef's delight; featuring stainless steel appliances, an island with gas stovetop and ample counter space for meal preparation. Entertaining is effortless in the cozy living room, where the second fireplace adds warmth and charm. The main level also includes two bedrooms, a full bath, and versatile spaces such as an office, den, or playroom, catering to your evolving needs. Upstairs, a private loft awaits, complete with a bedroom and full bath, offering ideal accommodation for guests or a teenager seeking a retreat. Storage is never an issue with the walk-in attic and expansive unfinished basement, which offers endless possibilities for a game room, workshop, or abundant storage space. Outside, the level lot provides ample space for outdoor activities and fun-filled gatherings. Located close to shops, restaurants, and the scenic Woodbury Trolley Trail. This home offers convenience and tranquility in equal measure.

42 Middle Quarter Rd, Woodbury

$470,000
3 Beds 3 Baths 24168924 MLS
Welcome to this beautifully maintained 3-bedroom, 3-bath high ranch nestled in the picturesque New England town of Woodbury. This inviting home offers a perfect blend of comfort, functionality, and modern updates. The upper level features gleaming hardwood floors throughout and an updated kitchen that flows seamlessly into an open-concept dining and living area-ideal for both everyday living and entertaining. New windows and a sliding glass door fill the space with natural light while providing easy access to the outdoors. Downstairs, you'll find a versatile lower level with durable laminate flooring, a full bathroom, and a private sauna-perfect for relaxation after a long day. Additional highlights include central air conditioning, an attached two-car garage, and a spacious primary bedroom complete with its own full bath. Set in a charming and desirable location, this home offers the best of New England living with modern conveniences.

5 Kimberly Ln, Woodbury

$465,000
3 Beds 3 Baths 24132918 MLS
Price Improvement for this Charming Country Retreat- A perfect alternative to Condo Living! Nestled on a serene 3 acre lot with picturesque stream, this property offers the tranquility of country living while maintaining easy access to nearby amenities. One level living- enjoy the convenience of the primary bedroom with spacious walk-in closet on the same level as the open floor plan kitchen/dining/livingroom. The lower level offers 1008 sq ft-above grade on three sides, with a full bath, large family room, office, and two additional bedrooms. Plenty of room to entertain family and friends. Both levels of the home are walkouts allowing for easy access to the outdoors and parking available at each level. Equipped with new high efficiency propane furnace and electric hot water heater, this home ensures reasonable energy costs and long-term reliability. Enjoy clean, safe drinking water with a reverse osmosis 5 filter water system at the kitchen sink. Custom built, 12' x 24' shed/garage with an overhead door that provides extra storage, workspace, or vehicle storage. This property is perfect for those seeking a peaceful lifestyle without the constraints of condo living. Whether you're looking to downsize or simply want a quiet retreat, this home offers the best of both worlds.

34 Transylvania Rd, Woodbury

$460,000
4 Beds 2 Baths 24129973 MLS
Welcome to this inviting 4-bedroom, 2 bath split level home offering the perfect blend of comfort and style. Step inside to a bright open floor plan featuring spacious living and dining areas, ideal for both relaxing and entertaining. The cozy fireplace creates a warm focal point while the large windows fill the home with natural light. The kitchen flows seamlessly into the dining and living area making everyday living and entertaining a breeze. The finished lower level provides extra flexibility-perfect for a family room office or guest suite. Enjoy outdoor living with 4.6 acres ideal for gatherings or quiet evenings at home. With its modern layout, great location and welcoming feel, this home checks all the boxes.

52 Scuppo Rd, Woodbury

$456,000
3 Beds 2 Baths 24075588 MLS
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 if perfect for gatherings, while the formal dining room offers ample space for entertaining. The kitchen has been thoughtfully updated with sleek granite countertops and durable engineered wood floors, providing a modern touch while maintaining the home's vintage appeal. The eat-in kitchen area features vaulted ceilings that add to its airy, spacious feel. It also comes equipped with a movable island, making it an ideal space for both everyday meals and entertaining. Upstairs you will find 3 generously sized bedrooms and a full bathroom. The half-bath on the main floor adds extra convenience for guests. Outside, enjoy a lovely porch with views of the street, while the backyard offers a private oasis with space for outdoor activities or relaxation. The detached one-car garage offers room for your vehicle and a separate area that can be used for hobbies, a workshop, or extra storage. With plenty of space for tools, craft supplies, or small projects, this versatile space is perfect for anyone needing extra room beyond the home.

50 Washington Rd, Woodbury

$452,000
3 Beds 1 Baths 24178085 MLS
Nestled along a country road on a cul-de-sac, this charming home offers the perfect blend of warmth, comfort, and convenience. A welcoming entry greets you with soaring ceilings, wood floors, and a propane stove that adds both character and cozy ambiance. The spacious country kitchen is designed for gathering, featuring vaulted ceilings, a large center island, stainless steel appliances, and an open feel ideal for entertaining family and friends. Just off the dining area, step down to an expansive patio - the perfect setting for morning coffee, summer picnics, or outdoor entertaining. Set on a full acre, the private front and back yards provide plenty of space for gardening, recreation, and relaxing in a peaceful setting. Just a few steps upstairs, the oversized primary bedroom offers generous space along with plumbing already in place for a future full bath. A large walk-in closet completes this inviting retreat. The full bathroom is conveniently located at the top of the stairs, easily accessible for guests and everyday living. A spacious two-car garage and nearby laundry area add to the home's functionality and convenience. Pride of ownership shines throughout this lovingly maintained, one-owner home. Enjoy country living with the convenience of being just minutes from shopping, schools, and commuter routes. Highest and best by Friday, 5/29 8PM.

104 Hard Hill Rd, Woodbury

$450,000
3 Beds 2 Baths 24156017 MLS
Price adjusted to accommodate cosmetic updates. Newer Beckett boiler, C/A, oil tank, and roof is approx. 9-10 years old! This unique, 1997 ranch-style home is set beautifully on nearly 2 acres of mostly level, private land with small pond in Historic Woodbury! The open floor plan of this home offers abundant natural light with a spacious eat-in kitchen, granite countertops, ample cabinetry, breakfast bar, and dining area perfect for gatherings throughout the year; especially with the large deck directly off the kitchen! There is also a large open living room that provides a comfortable space for relaxing and conveniently leads to the primary suite featuring a walk-in closet, soaking tub, separate shower, and double sinks. Two additional bedrooms and a full bath are located on the opposite side of the home. A spacious and open foyer leads to an enormous unfinished walk-up attic with great potential for future expansion that could easily double the square footage of this home! Wow! You will love this space and all the possibilities! The partially finished walkout basement is not included in the square footage and offers additional flexible living space ideal for a home office, gym, or whatever your needs are. Downstairs also includes a laundry area and plenty of storage with convenient access to the 2-car garage. Outside, enjoy a large yard to run and play in, an oversized deck great for cookouts and entertaining, plenty of space for gardens, gorgeous trees for privacy, etc

133 White Deer Rocks Rd, Woodbury

$449,900
4 Beds 4 Baths 24068239 MLS
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 garage doors. The kitchen and hallway feature new vinyl plank flooring. Systems improvements include a new gas-fired direct vent water heater, a new central air condenser, and updates to the well and septic systems - including a new sanitary well cover, water filters, septic outlet cover, distribution box, and added water softener discharge field. Two-car attached garage. The primary bedroom includes a full bathroom. This home blends a functional layout with substantial updates inside and out. HVAC, Termite Inspection, Roof Inspection, Well Inspection/Water Test & Septic Inspection completed. This property is eligible under the Freddie Mac First Look Initiative through 07/21/2025. See agent remarks on offer submission. Property to be sold in as-is condition.

67 Flanders Rd, Woodbury

$445,000
3 Beds 2 Baths 24066265 MLS
Enjoy life near the clouds with amazing mile-long views of the hilltops from your private getaway. This home, located on the Woodbury skyline, provides a comfortable and peaceful place to live. The single-story design features hardwood floors and three large bedrooms, including a primary suite with its own full bathroom. The open living and dining area includes a wood-burning fireplace, perfect for relaxing or spending time with family and friends. Downstairs, the finished lower level has a walkout door, a wood stove, and plenty of space for a cozy hangout or home office. The two-car garage provides extra storage and easy access. Outside, the two-tiered deck is a great spot to unwind, entertain, or simply enjoy the quiet surroundings. Set apart from the neighbors, this home enjoys privacy and beautiful views.

397 Railtree Hill Rd, Woodbury

$442,500
3 Beds 2 Baths 24014614 MLS
So much opportunity here! 13 Acres backs to 38 acres owned by the Regina Laudis Abbey. Feasibility study done & attached. Shows two potential choices. Keep the 3 BR house - (rebuilt and added onto in 2013)- on 2.38 acres and subdivide w 2 large additional 5 acre lots, this leaves 4 acres of open space or keep the house on 7.79 acres and create an 8.5 acre lot. OR keep it all with the house for a family compound! Live in home while building your dream house then keep this home as a rental ? Keep it all as one and use the 13 acres for animals, quads, or hunting? Small pond on property, some trails established for quads/dirt bikes. Lot's of options here. Drive thru Flanders Nature Center preserve over Cowles Road for a really beautiful ride home. This one of the few rural dirt roads left in town, (this end is paved) peaceful, nature filled location, yet close to Woodbury and Bethlehem town centers. Barn structure is unsure - please do not enter top floor - you can open door and look inside. Def needs a roof. Lower level has stone foundation and was used more recently to house goats. Appears sound. Subdivision not completed, only feasibility.

325 Cowles Rd, Woodbury

$440,000
3 Beds 3 Baths 24174349 MLS
** Multiple offers highest and best 5/17 5pm**Tucked away on 4.99 serene wooded acres in picturesque Woodbury, this solidly built Cape Cod offers privacy, charm, and endless potential. Surrounded by mature trees and peaceful natural beauty, the property provides a true country setting with room to create gardens, walking trails, or space for animals and hobby farm interests. Inside, the home features 3 bedrooms, 1.5 baths, beautiful hardwood floors, and a warm, inviting layout filled with timeless character. Whether you envision restoring its classic charm or creating your own private retreat, this property offers a rare opportunity to own nearly five acres in one of Litchfield County's most sought-after towns.

89 Lighthouse Rd, Woodbury

$440,000
3 Beds 2 Baths 24052454 MLS
Hotchkissville Gem. This elegantly restored home features enchanting period details and low-maintenance living in a central location. The perennial-lined front yard is framed by stone and split-rail fencing. Step inside to an inviting stone-floored mudroom with a built-in granite bench, leading to a classic eat-in kitchen with a windowed alcove and custom pantries. The dining room showcases plaster-finished walls and wide board flooring, ideal for entertaining, flowing seamlessly into the living room with its oversized fireplace and built-ins, creating a warm atmosphere for gatherings. Upstairs, the primary suite offers a vaulted beamed ceiling, a full bath, and two walk-in closets, complemented by two additional pass-through bedrooms. Enjoy stunning views of neighboring meadows. With a detached garage, Viessmann furnace and central air on the second level, this home beautifully combines comfort and country living. Don't miss this exquisite escape!

236 Quassuk Rd, Woodbury

$440,000
4 Beds 3 Baths 24025489 MLS
A property that has it all and then some. You get a home with plenty of living space, a main floor primary suite, warm neighborhood, 4.64 acres, private walking/hiking trails off the back of the home, a large back deck, good size pantry and so much more. Close enough to the quintessential heart of Woodbury yet country enough to appreciate the serenity. Come in and enjoy the charming grand living room with a propane fireplace and open floor plan with a soaring ceiling. Also on the main level is an office nicely situated near the half bathroom and kitchen. The remaining three bedrooms are on the second floor with a shared bathroom along with a sizable storage closet and catwalk to a room that is ready to be finished if you desire. The lower level has been partially started and easily could be completed for more living space or desirable storage. This home is a gem providing all the feels of the country while being easily in close proximity to stores, restaurants antique shopping and home town festivities. Come see this one you will love it.

990 Washington Rd, Woodbury

$440,000
4 Beds 2 Baths 24024980 MLS
A peaceful oasis on over 4.6 acres, this split level home has so much to offer the home owner who values privacy. This home welcomes you with vaulted ceilings and an open floorplan. As you enter, you will notice the hardwood floors throughout, the light and bright kitchen with SS appliances, and the cozy fireplace in the living space. The upper level is complete with two bedrooms and two full bathrooms, all well-maintained. The lower level offers plenty of space for a rec room and provides any additional space you may need. Here you will also find the laundry hookups. Outside, the home has been well kept. You can enjoy the private outdoors on the patio and you have plenty of yard to entertain. Two car garage provides extra storage space plus ample parking space in the driveway is available.

52 Scuppo Rd, Woodbury

$440,000
3 Beds 3 Baths 170581731 MLS
Wonderful 3BR New England Cape, lovingly maintained, just minutes to Flanders Nature Center & Land Trust. Offering easy living with a great floor plan and comfortable living spaces. Large, sunny kitchen with spacious breakfast nook (with built-in benches), LVP flooring, and pantry. Living room with wood flooring and stone fireplace. Elegant dining room. Main level office (or den). Upstairs you’ll find the ensuite primary bedroom with large walk-in closet; two additional guest bedrooms (one with walk-in closet) and hall bathroom. The lower level is a walk-out and offers great potential to finish. Lots of storage too. The covered deck (just painted) is perfect for dining outside. The rear yard has plenty of space for gardening and/or entertaining. Detached 2 car garage. Central air. New well tank 2021. Vinyl siding. Generator hook-up. Great location just minutes to the center of town. Enjoy wonderful restaurants, antique shopping, an array of community activities, parades and more!

79 Flanders Rd, Woodbury

$436,000
3 Beds 2 Baths 24163332 MLS
Highest and Best by 04/07 at 5:00pm. Beautiful 3-bedroom, 2-bath home located in the heart of Woodbury. Currently the only raised ranch on the market, this property offers a wonderful opportunity in a highly desirable area. The home features a level yard, perfect for outdoor enjoyment, along with a fully finished basement complete with a full bath-ideal for entertaining or providing comfortable space for guests. The main level includes three generously sized bedrooms, a welcoming living room with a fireplace, and a dining area filled with natural light. Additional highlights include a 2-car garage and central air for year-round comfort. Conveniently located near schools and shopping, this home is set in a truly quiet neighborhood-let's just say the neighbors won't be making much noise.

40 Church St, Woodbury

$435,000
3 Beds 3 Baths 170624521 MLS
Escape to your serene country retreat! This captivating home boasts three cozy bedrooms, including one full bathroom and two convenient half bathrooms, seamlessly blending rustic charm with modern comforts. Custom wood flooring welcomes you into the open-concept main level, where a woodstove enhances the inviting living space. The updated kitchen features stainless steel appliances, butcher block countertops, and charming reclaimed barn wood accents, while the expansive upper-level deck overlooks the mostly level yard, perfect for outdoor gatherings. Upstairs, three tranquil bedrooms await, complemented by an updated full bathroom. The full basement offers entertainment potential with a trendy bar and walk-out access to the backyard—a haven for summer BBQs and joyful gatherings. Embrace the tranquility of country living in this must-see home. Schedule your private tour today and experience the magic firsthand.

203 Carmel Hill Rd, Woodbury

$430,000
3 Beds 2 Baths 24179907 MLS
Welcome home to this charming 3-bedroom, 2-bath ranch, perfectly situated on a lovely lot. This home offers comfortable one-level living with a bright and inviting floor plan designed for everyday living and entertaining. The spacious living areas flow seamlessly into the kitchen and dining space, while three generously sized bedrooms provide ample room for family, guests, or a home office. Enjoy the convenience of two full baths and the beauty of the outdoor setting, featuring a private backyard ideal for relaxing, gardening, or hosting gatherings. The oversized two car garage allows for plenty of storage. This is your chance to live in the beautiful and desirable town of Woodbury. This home is being sold AS IS.

134 Old Sherman Hill Rd, Woodbury

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