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520 Washington Rd, Woodbury
$547,500
3 Beds ⋅ 2 Baths ⋅ 24191493 MLS
Classic 1800s vintage Colonial in Connecticut's most charming town! Located within a short drive of all major conveniences, area private/public schools and parks, this three bedroom, two bath home has something for everyone! Situated on a beautifully level lot, enjoy your 1.55 acres by throwing the ball around, entertaining on your slate side patio or terrace area. The backyard barn, named the "Carriage House", is a unique feature of the property that is just waiting for you to cultivate your favorite hobby. On the main level of the home you will find a spacious country kitchen with hook up for a woodstove. The formal dining room can fit the relatives for the upcoming holiday season, and the formal living room, with center fireplace, beams with natural light! Rounding out the first floor is a study with custom-built bookcases and a full bath off the kitchen. Upstairs are spacious bedrooms, a full bath with clawfoot tub, and a bonus room, currently used as another bedroom. Lastly, the walk up attic is fully floored and highly functional for your storage needs or other use. Come and appreciate how this property reflects Woodbury's 19th century antique flair!

520 Washington Rd, Woodbury
105 Minortown Rd, Woodbury
$545,000
3 Beds ⋅ 3 Baths ⋅ 24102573 MLS
NEW PRICE! Don't wait! This ranch-style home might be the perfect fit! Just minutes from town, the property offers a variety of opportunities. The main level features three bedrooms, two bathrooms, a living room with a gas log fireplace, a formal dining room, and a spacious eat-in kitchen. The partially finished lower level includes a family room, office space, and a full bath. Built in 2008, the garage barn provides ample space for four cars, a workshop, and a studio space above. You can also create a path down to the Nonnewaug River for more outdoor fun. House needs some TLC so bring your ideas! Come and enjoy all that Litchfield County has to offer, just 90 minutes from NYC.

105 Minortown Rd, Woodbury
12 Walker Rd, Woodbury
$540,000
3 Beds ⋅ 3 Baths ⋅ 24179773 MLS
Would you like to live in beautiful Woodbury Connecticut. Set on 1.95 acres of peaceful, private grounds, this beautifully updated 3-bedroom, 2.1-bath home sits gracefully on a gentle rise at the top of the driveway, partially framed by classic white post and rail fencing that enhances its New England charm. The entire home-interior, exterior, trim, and baseboards-has been freshly painted, move-in-ready feel. Inside, you'll find hardwood flooring throughout, complemented by brand new LVP flooring in the expansive kitchen, central air and a Generac generator system. The kitchen offers an abundance of dining and workspace, a walk-in pantry, and brand-new stove and dishwasher. An oversized two car garage with newer doors provides excellent storage and convenience. The full, unfinished basement offers tremendous potential, complete with two additional storage rooms ideal for organization or future expansion. Outdoors, the setting is serene and usable, with mature trees, open lawn space, and two bonus structures: an additional shed and a separate garage building, perfect for hobbies, equipment, or extra storage. Located in picturesque Woodbury-known for its antique charm, farm to table dining, and scenic countryside-this property offers privacy, updates, and room to grow. Trustee selling, so no disclosures - being sold "AS IS" Cameras in use do NOT go onto the property without an appointment - Under ground Oil tank was discovered will be removed by closing

12 Walker Rd, Woodbury
18 Woodbury Hill, Unit 18, Woodbury
$540,000
2 Beds ⋅ 3 Baths ⋅ 24133803 MLS
Experience the charm of Woodbury's most desirable condominium community at 18 Woodbury Hill. This beautifully updated Putnam's Loft model offers an open and inviting floor plan perfect for both everyday living and entertaining. The main level features a spacious living room with oak floors, vaulted ceiling, fireplace, and abundant natural light, flowing seamlessly into the dining room. The renovated kitchen opens to an expansive private deck, complete with stairs to the landscaped rear yard and lush plantings. The first-floor primary suite includes a walk-in closet and a stylishly updated bath, providing the ease of one-level living. Upstairs, a versatile loft with built-ins, a second bedroom, and a full bath create the ideal space for guests, a home office, or a playroom. Additional highlights include a huge finished closet over the two-car garage, a full basement with two cedar closets and extensive shelving, and plenty of storage throughout. Residents of Woodbury Hill enjoy exceptional amenities, including a pool, tennis courts, and a prime location just minutes from downtown shops, dining, and major routes. This special unit combines modern updates, thoughtful storage, and serene outdoor living-making it a wonderful place to call home.

18 Woodbury Hill, Unit 18, Woodbury
106 Sprain Brook Rd, Woodbury
$535,000
3 Beds ⋅ 2 Baths ⋅ 24189823 MLS
Welcome home to this charming farmhouse setting with privacy and room to grow. The open flat acreage boasts a 2 stall barn with power ready for a hobby farm, or reimagined as a potential pool house, art studio or potential guest quarters. The 3 bedroom 2 full bath home is set overlooking the land and barn with spectacular views from the deck. The long private driveway and peaceful location gives that countryside feeling without being remote. There is space for gardens, animals, or just wide open sky. This special property brings farmhouse living with modern possibilities.

106 Sprain Brook Rd, Woodbury
31 Mcveigh Rd, Woodbury
$530,000
4 Beds ⋅ 3 Baths ⋅ 24130855 MLS
Welcome home to 31 McVeigh Rd! Privately set on 1.70 acres in the Quassapaug neighborhood, this home blends comfort, efficiency, and convenience. The living room offers a wood-burning fireplace, while a 2019 high-efficiency wood stove in the family room adds warmth and helps lower heating costs. The main level features connected yet distinct spaces-living room, family room, dining area, and a kitchen with backyard views that offers lots of cabinet space, granite countertops and an island perfect for meal prep. Sliding doors off the family room open to a deck and screened gazebo with electricity and ceiling fan, ideal for relaxing or entertaining. Upstairs are four bedrooms with ample closets, including a primary suite with new carpet, walk-in closet, and full bath. The finished lower level provides flex space and direct access to the oversized two-car garage with new doors and storage. Minutes from Lake Quassapaug, Woodbury's downtown, shopping, and I-84

31 Mcveigh Rd, Woodbury
212 Upper Grassy Hill, Woodbury
$525,000
3 Beds ⋅ 2 Baths ⋅ 24189460 MLS
Well maintained and updated Raised Ranch 3 bedroom 1.5 bathrooms home ready to move in! Open concept living room/dining room and kitchen that opens on to a gorgeous 12'x30' deck overlooking a beautiful fenced in backyard in the woods make for a very private setting. This home has all new windows, a newly updated kitchen with stainless steel appliances and granite countertops, finished lower-level ideal for home office or living space with plenty of natural light, windows and recessed lighting. Cutting edge solar panels save on electric bill! Conveniently located close to all amenities, shopping, dining, and major highways. Enjoy all that Woodbury has to offer - rated best town by Yankee Magazine. "Sold as is condition" a must see!

212 Upper Grassy Hill, Woodbury
63 Woodbury Hill, Unit 63, Woodbury
$525,000
2 Beds ⋅ 3 Baths ⋅ 24171961 MLS ⋅ Woodbury Hill BLDG.
Exceptionally private, Putnam Loft model in the sought after Woodbury Hill! This unit is located in a secluded part of the community with woods behind and only sounds of the nearby babbling brook. This well-cared for unit features hardwood floors throughout, vaulted ceilings, floor to ceiling gas fireplace, a large dining room and remodeled kitchen. The primary bedroom suite is on the main level and includes, full bath, walk-in closet with access to the washer/dryer as well as the garage. Upstairs find a large loft perfect as a reading room, study or home office, which offers great natural light pouring through its skylights. An additional full bath and bedroom are located on this level to easily accommodate an out of town guest or another family member. Recent updates include a new HVAC system and fireplace gas insert. The currently unfinished basement with walk out to the stone patio can be used for storage or can be easily finished with its suitable ceiling height and built-in windows and slider. There is additional storage in the upstairs eaves of the second bedroom or off the loft area. Schedule your showing now while this stunning and private unit is still available!

63 Woodbury Hill, Unit 63, Woodbury
667 Upper Grassy Hill, Woodbury
$522,500
4 Beds ⋅ 2 Baths ⋅ 24142886 MLS
Discover this meticulously maintained Cape-style home set on 3.4 private acres in Woodbury. The property offers exceptional curb appeal, featuring a paved circular driveway and a classic stone wall that sets a welcoming tone. Inside, a beautiful slate tile foyer opens to hardwood floors and a comfortable, well-designed layout that creates an inviting atmosphere. The main level includes a generously sized living room, a dining room with a pellet stove and an elegant bow window, and an eat-in kitchen. This level also offers two bedrooms with ample closet space and a full bathroom. Adjacent to the kitchen and dining area is a spacious, heated sunroom filled with natural light-an ideal spot for relaxation.The upper level features two additional bedrooms with hardwood floors, another full bathroom, and a versatile mixed-use room which works nicely for crafts, storage, or additional closet space. Outdoors, a nicely appointed deck offers the perfect place to unwind and enjoy the serene surroundings. The property also includes a detached two-car garage with overhead storage, ideal for tools, hobbies, or additional equipment. If you're seeking a comfortable home that offers space, privacy, and a peaceful setting, this property is certainly worth your consideration.

667 Upper Grassy Hill, Woodbury
437 Middle Road Tpke, Woodbury
$517,000
3 Beds ⋅ 2 Baths ⋅ 24173270 MLS
Everything has already been done for you. Just move in, unpack, and enjoy the ease of single-floor living in this beautifully renovated ranch with endless potential below. Completely renovated and truly move-in ready, this home offers effortless living with every major updated already completed. From the brand-new HVAC system and newly installed septic to new windows, lighting, interior and exterior paint, driveway, and front walkway, this property has been thoughtfully upgraded from top to bottom. At the heart of the home is a stunning new kitchen that opens seamlessly to the dining and living areas, creating the perfect flow for both everyday comfort and entertaining. The beautifully updated fireplace with new stonework and a floating mantel adds warmth and character, while all-new bathrooms bring a fresh, modern feel throughout. And don't let the size fool you - the expansive unfinished basement significantly increases the home's potential. Complete with a newly updated half bath, this lower level offers an incredible opportunity to create additional living space, whether you envision a family room, home office, gym, guest suite, or playroom. Outside, the expansive yard provides plenty of space to relax, entertain, or enjoy the outdoors. Turnkey, low-maintenance, and full of future possibilities, this home offers the perfect combination of comfort, convenience, and room to grow.

437 Middle Road Tpke, Woodbury
43 Bethwood Ln, Woodbury
$513,999
3 Beds ⋅ 2 Baths ⋅ 24171809 MLS
If you're looking for your own piece of heaven, this may be it. Hard to find and full of potential, this modest single-level home is set on a secluded 5+ acre parcel of gorgeous open meadow. Located on a private road near the Woodbury/Bethlehem line, the home offers three bedrooms, an eat-in kitchen, dining room, living room with fireplace, breezeway, and an attached two-car garage. With only a step or two from parking to the living area, the layout provides easy single-level living. The home is set back from the road, providing distant views, abundant meadowland, and wonderful privacy from neighbors. The property is ideal for raising animals, building a workshop, creating expansive gardens, or simply enjoying the peace and open space. While the interior needs some TLC, the current owners have already upgraded several major items, including a new roof, new furnace, and new oil tank. For the right person, the remaining work is manageable, and the outcome could be a true gem for years to come.

43 Bethwood Ln, Woodbury
242 Bacon Pond Rd, Woodbury
$513,000
4 Beds ⋅ 2 Baths ⋅ 24162107 MLS
Charming antique two-family property in the heart of Woodbury featuring a main residence plus a separate legal apartment over the detached 2-car garage-ideal for rental income, in-law setup, or owner-occupant flexibility. The main home offers 3 bedrooms, 1 bath, wide board antique flooring, original built-ins, and three fireplaces, including one in the cozy eat-in kitchen. The apartment provides approximately 700 sq ft of additional living space with a full bath and private setting. Set on a beautiful 1.46-acre treed lot with gardens, irrigation, and open space. Convenient in-town location close to shopping, dining, and commuter routes.

242 Bacon Pond Rd, Woodbury
14 Meadow Crest Dr, Woodbury
$500,000
3 Beds ⋅ 2 Baths ⋅ 24149855 MLS
Opportunity knocks! Your chance to reside in an exclusive cul-de-sac area of north Woodbury! Homes on this street rarely come on the market. Situated on almost 4.5 acres and within a short drive of Woodbury and Watertown centers, including prestigious, private Taft School, this three bedroom, 1.5 bath colonial awaits its new owners! Exterior features include a chicken coop, above ground pool, jacuzzi, mature plantings and an extended process driveway making a portion of the back acreage accessible. Upon entering the home, you are greeted by a classic center hall foyer. Spacious dining and family rooms surround the foyer, along with a cozy sitting room, and a sun-filled bonus room with walk out to the side patio. A remodeled half bath and a country-kitchen, with newer appliances, complete the first floor. On the second level, find three spacious bedrooms, an additional room for home office or crafting space, and a remodeled full bath with walk-in shower and soaking tub. The lower level offers partially finished space, a laundry area, and plenty of room for storage. The two car attached garage has floored loft space for your additional storage needs. Some minor finishing touches are needed in the home. Get ready to enjoy the quiet life, where the only sounds you will hear are the ones that nature provides!

14 Meadow Crest Dr, Woodbury
9 Hill View Ln, Woodbury
$500,000
2 Beds ⋅ 3 Baths ⋅ 24143007 MLS
Charming Dutch Colonial located in the desirable South Brook community in Woodbury, walking distance from the bustling shops and restaurants. This home is part of a small enclave of 21 single, detached residences. Features include a new wood roof, hardwood floors throughout, and a private backyard with patio. The first floor offers a formal dining room, an eat-in kitchen with ample cabinet and storage space, and a step-down family room with vaulted ceiling, built-in bookcases, and a fireplace. The primary bedroom suite includes walk-in closets, a jetted tub, and a stall shower. An office completes the first floor. The second floor includes a second primary suite with full bath, an additional room ideal for an office, guest space, or playroom, and a den/second family room. The partially finished basement features a game room with the pool table included, plus additional storage areas. South Brook is pet-friendly and not age-restricted. HOA services include garbage, lawn and tree care, snow removal, fertilizing, and leaf blowing. Two pets with no size restriction are allowed as well! The property is equipped with an electric fence around the yard perimeter. So much to love, space, convenience, and low-maintenance living in a sought-after location.

9 Hill View Ln, Woodbury
12 Spring St, Woodbury
$500,000
3 Beds ⋅ 2 Baths ⋅ 24121873 MLS
Step into this well-cared-for 3 bedroom, 2 bath Victorian offering just over 2,000 sq. ft. of comfortable living space. Filled with natural light and character, this home blends historic charm with thoughtful updates, including a mix of original and newer engineered hardwood floors, and two generously sized, updated baths. Original architectural details add warmth and personality, while newer features- like energy efficient windows and a brand new washer and dryer- make everyday living easy. You'll find spacious living and dining rooms perfect for gathering, plus a main level office that's ideal for working from home or flexible use. Upstairs, there are 3 bedrooms and a cozy multi-use room which makes a great reading nook, playroom, or creative space- and even has access to an beautiful upper-level porch, ideal for a quiet escape. The classic covered porch is a welcoming spot to relax with a morning coffee, and the fenced in yard offers plenty of room to garden, play or entertain. A detached two-car garage adds even more value with assorted tools, lawnmower and snowblower which are all included in the sale! Tucked on a quiet street just off Main, you're close to shops, restaurants, parks, town sidewalks and everything else downtown has to offer. Schedule your showing today!

12 Spring St, Woodbury
17 Old Flanders Rd, Woodbury
$490,000
3 Beds ⋅ 3 Baths ⋅ 24135694 MLS
Welcome to this beautifully situated saltbox colonial reproduction home that perfectly blends privacy and a cul-de-sac neighborhood setting. Step into the inviting cathedral foyer flooded by natural light from the two skylights above. The first floor features rustic wide board pine floors that complement the stone fireplace in the living room for a classic New England feel. The sunny kitchen has a skylight and four windows situated over granite countertops and stainless steel appliances. The dining room has French doors opening to the multi-level cedar deck. Also on the first floor is a half bath, laundry room and the spacious primary bedroom with ensuite full size bathroom. Upstairs find two additional bedrooms and full size bathroom. Each bedroom has ample closet space and pull-down attic steps offer additional storage space. Recent updates include a new roof and plywood sheathing, siding and exterior paint and a well pressure tank, all completed in 2020-2021. The German-made Viessmann boiler with three-zone heating ensures comfort and efficiency. Room for multiple vehicles in oversized two car garage with dual openers and paved driveway. This home offers the chance to move into a desirable Woodbury neighborhood while planning your updates, making it an excellent opportunity to grow your investment over the years.

17 Old Flanders Rd, Woodbury
15 Lynns Corner Rd, Woodbury
$490,000
4 Beds ⋅ 3 Baths ⋅ 24135164 MLS
Set along a private driveway and conveniently located near the town centers of Woodbury, Bethlehem, and Watertown, this contemporary-style Cape blends charm, character, and modern updates throughout. The open-concept kitchen and living room feature granite countertops, stainless steel appliances, and a slider leading to a spacious deck overlooking a lush yard and babbling brook - perfect for morning coffee or evening unwinding. The main level includes a dining room, full bath, and a flexible bedroom ideal for guests or a home office. Upstairs, the primary bedroom offers a walk-in closet and a newly remodeled balcony with peaceful views of the backyard. A fully renovated bath with a walk-in tile shower and linen closet serves two additional upstairs bedrooms, each full of character. The walkout lower level is partially finished with a laundry area, full bath, and space for a potential in-law setup, or studio- all with a separate entrance. Additional highlights include new luxury vinyl plank flooring, propane heat, central air, and town-approved permits for a 20x24 garage. The site has already been cleared and prepped for future use. Thoughtful updates, inviting spaces, and tranquil surroundings make this a standout home - ready to welcome its next chapter.

15 Lynns Corner Rd, Woodbury
74 Woodbury Hill, Unit 74, Woodbury
$489,000
2 Beds ⋅ 3 Baths ⋅ 24146027 MLS ⋅ Woodbury Hill BLDG.
Beautiful Woodbury Hill condo located in a desirable, small, and quiet complex offering a rural setting with convenient access to town. Ideally positioned within the community, the unit is an easy walk to the tennis/pickleball courts and saltwater pool. The home features 2 bedrooms and 2.5 baths, an updated kitchen, dining room, living room, powder room, loft and finished lower level. The removal of the hall wall transformed the living room with cathedral ceiling and wood fireplace to an open and airy space. The formal dining room overlooks the rear yard and a picturesque horse farm beyond. The kitchen has been updated with newer GE and Bosch appliances. A set of sliders leads from the kitchen to the oversized deck. The upper loft with skylight and vaulted ceiling and the finished 667 sq ft lower level complete the public rooms. The first-floor primary bedroom has a walk-in closet and full bath, while the upper level offers a guest bedroom with walk-in closet and its own bath. There are ample storage spaces and an attached two bay garage. Located in Woodbury, CT-named Reader's Digest "Most Charming Small Town" three times. Enjoy nearby restaurants, galleries, cultural venues, day spas, hiking trails, ski areas, wineries, and equestrian facilities. Approximately 90 minutes from Manhattan.

74 Woodbury Hill, Unit 74, Woodbury
145 Cat Swamp 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
38 Mountain Rd, 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
5 Kimberly Ln, 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
34 Transylvania Rd, 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
52 Scuppo 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
104 Hard Hill 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
133 White Deer Rocks 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
89 Lighthouse 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
40 Church St, 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
9 Spring St, Woodbury
$435,000
3 Beds ⋅ 2 Baths ⋅ 24186179 MLS
Warm and welcoming, this vintage home with a classic rocking chair front porch is ideally located within walking distance of Woodbury's town center. Beautifully maintained, it blends timeless character with thoughtful updates throughout. A gracious foyer with hardwood floors and a wall of closets provides exceptional storage. The living room features hardwood floors, built-in shelving, and an electric fireplace, while the dining room showcases a classic built-in cupboard. The updated country kitchen offers Vermont soapstone countertops and new flooring, and a convenient main-level laundry room with a half bath completes the first floor. Upstairs are three bedrooms and a full bath. Energy-efficient improvements include newer windows and doors, along with individual thermostats in every room for personalized comfort. An enclosed rear porch provides the perfect mudroom or everyday entry. Outside, the level backyard has been transformed into a park-like retreat with a new patio, attractive landscaping, and plenty of space for entertaining, gardening, or simply relaxing. A shed provides additional outdoor storage. Located in Woodbury, named Reader's Digest's "Most Charming Small Town" three times, this home offers easy access to restaurants, galleries, cultural venues, day spas, hiking trails, ski areas, wineries, and equestrian facilities. Approximately 90 minutes from Manhattan, it offers the perfect blend of small-town charm and convenience. Seller reviewing offers.

9 Spring St, Woodbury
134 Old Sherman 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
43 Woodbury Hill, Unit 43, Woodbury
$430,000
2 Beds ⋅ 2 Baths ⋅ 24170943 MLS ⋅ Woodbury Hill BLDG.
Rarely is a ranch style available at Woodbury Hill as there are only 7 in total, This one is almost self standing-neighbor's one car garage is adjacent to this two car garage. There is an additional 640 sq.ft. in the heated lower level with a laundry room, closets, half bath and a separate work area and all with sliders to the yard. The beamed living/dining room is cathedral in the living room section with a two story window and lovely fireplace. A nice sunny den is nearby and down the hallway is the MBR with a slider to the wrap around deck. There are two full baths on the main floor. The large kitchen also has a slider to the oversized deck that shows beautiful views of the grounds. Keep in mind that Woodbury Hill is in walking distance to the center of Woodury which includes the library, stores, post office, parks, community center for exercise classes and lectures. Take advantage of the outdoor pool, tennis court and gatherings at the gazebo. Enjoy the award winning restaurants, golf courses, nature centers, community theater, art galleries and antique shops. Remember you are only minutes from major routes and 1 1/2 hours to NYC by car and 1/2 hour to the train. This lovingly cared for home is easy to show and well worth it. Woodbury was listed as No.3 in the 10 places to live in Connecticut according to Travel and Leisure as seen in the May issue of Ct. Magazine.

43 Woodbury Hill, Unit 43, Woodbury

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