Refine Search
Map
Sort by
$675,000
5 Beds ⋅ 5 Baths ⋅ 170615767 MLS
Wonderful opportunity to own a charming 4-bedroom New England Cape with 1 bedroom in-law or guest apartment in a quiet and convenient section of Woodbury. Built and loved by the current owners for the past 62 years. The main residence includes the kitchen, formal dining room, formal living room with pellet stove, office, two bedrooms and full bath, all on main floor. There also is a second full bath with laundry. The upper level includes two bedrooms and a full bath. The lower level includes a rec room with a fireplace and another finished room with wet bar. The wall separating the two can be removed to make one big room. The in-law is spacious and feels like a house of its own. On the main floor is a living room with hardwood, half bath, spacious eat-in kitchen with laundry, and the bedroom with full bath, built-ins, bookshelves, and walk-in closet. Upstairs is an office with full bath and den or sitting area with built-ins. The main residence is heated by a newer oil boiler and the apartment uses propane for heat, water, and cooking with 500 gallon buried propane tank. With many rooms, the house allows multiple configurations. The yard is enchanting with multiple porches, stone patios, stonewalls, gardens and plenty of lawn. Bring your dreams and ideas to make this special property your very own. Property is being sold as-is.

9 Meadow Ave, Woodbury
$670,000
3 Beds ⋅ 2 Baths ⋅ 24105910 MLS
Please submit all highest and best offers by 3:30pm today 6/28. Welcome to 50 Elephant Rock Road - a hidden, otherworldly retreat tucked away in one of Litchfield County's most desirable historic towns. Towering rock formations, the setting's namesake, and lush park-like gardens provide an idyllic, "nestled in" feeling of serenity and seclusion the moment you arrive. Stone walls and brick pathways meander through beautifully landscaped grounds to a show-stopping, free-form gunite pool. Framed by natural fieldstone and manicured hedges, it offers both privacy and elegance, ideal for lazy cottage summer days or unforgettable gatherings. The home has been thoughtfully renovated with a bright, welcoming living room anchored by a refreshed fireplace and thoughtful details throughout. A smart new layout includes three bedrooms and two full baths, both featuring radiant heated floors, and beautifully considered design elements that marry charm with contemporary touches. This rare blend of peaceful beauty, modern comfort, and timeless character is truly one-of-a-kind-50 Elephant Rock Road is special- discover for yourself!

50 Elephant Rock Rd, Woodbury
$665,000
4 Beds ⋅ 3 Baths ⋅ 24160671 MLS
Welcome to 74 Middle Quarter Rd-minutes from downtown, a charming antique colonial home that has been truly loved and thoughtfully maintained, offering the perfect blend of character, space, and everyday comfort. From the moment you step inside, you'll feel the warmth of the main level, featuring a farmhouse-style kitchen with an eat-in area and a cozy wood-burning stove-the kind of space where everyone naturally gathers. The oversized family room, formal dining room, and inviting living room provide plenty of room to spread out, while the central conversation lounge creates a unique and welcoming heart of the home. Upstairs, you'll find four generously sized bedrooms, including a primary suite with a walk-in closet and full bath. An extra living space offers flexibility for a playroom, den, or TV room-whatever fits your lifestyle. The upstairs laundry room is as practical as it is spacious, complete with abundant storage, a wash sink, and even a cedar closet. Need more space? The walk-up attic includes a partially finished area perfect for a home office, creative space, or additional storage. Set on 4.7 peaceful acres, this property invites you to slow down and enjoy quiet evenings and the beauty of nature. The 3-car garage includes an unfinished upper level with endless potential, plus two additional sheds for even more storage. And the surprise you didn't know you needed-owned solar panels keeping electric costs incredibly low (avg just $20/month). Book your showing

74 Middle Quarter Rd, Woodbury
$665,000
4 Beds ⋅ 3 Baths ⋅ 24130704 MLS
Nestled on approximately 5.38 acres of lush, mature landscaping, this captivating house offers an abundance of space and tranquility. The property features four bedrooms and three bathrooms, spanning approximately 3,064 square feet of thoughtfully designed living space. The expansive, spacious lot is complemented by a serene outdoor space, boasting a paved patio, a spacious deck, and a sprawling, lush backyard. Mature trees and a scenic landscape create a natural, serene ambiance, while the inviting outdoor space and ample natural light throughout the home foster a harmonious living experience. Inside, the home showcases hardwood flooring, vaulted ceilings, and a stone fireplace, exemplifying elegant finishes. The spacious kitchen is equipped with granite countertops, providing ample meal preparation space. The bathrooms feature elegant tile work and ample natural lighting, creating a spa-like atmosphere. The layout of the home is thoughtfully designed, offering a spacious entryway and an abundance of natural light throughout the living spaces. The primary bedroom and additional bedrooms provide comfort and privacy, while the hardwood floors, arched windows, and other distinctive architectural elements add to the home's charm and character. Woodbury is a good place to live for those who appreciate a quaint, historic New England town with a strong community feel, a focus on local businesses, and plentiful outdoor activities. NEW ROOF BEING INSTALLED AND 1 YEAR HOME WARRAN

174 Weekeepeemee Rd, Woodbury
$665,000
3 Beds ⋅ 3 Baths ⋅ 170593850 MLS
This meticulously crafted reproduction Cape is a true gem in the heart of Litchfield County. Nestled on just over 2 acres of land, this property offers a serene and timeless escape. The home boasts wide board floors and plaster walls, providing an authentic vintage feel, combined with modern comforts. With all your daily essentials on the main floor, this home offers convenient and comfortable one-level living with over 3400 square feet.The open-concept living/dining areas are perfect for entertaining, with a cozy paneled wall fireplace for those New England winters.The well-appointed kitchen features modern appliances with an expansive wall of windows. A sunroom with radiant heat provides a retreat to read a book, relax with your morning coffee or work from home. The main level includes a spacious master suite, complete with a walk in closet and en-suite bathroom. Upstairs, you'll find 2 additional bedrooms each with character and a large sitting area in the main hall. An additional 500+- sq ft unfinished room would make a great home office. Step outside to the lush, low maintenance grounds. The backyard offers endless possibilities for gardening, outdoor activities, or simply enjoying the natural beauty. This home provides a serene retreat while being conveniently located near shops, award winning restaurants, antique shops as well as being close to train stations and 90 minutes to NYC. Don't miss out on what Readers Digest named Woodbury as the "Most charming small towns"

165 Grassy Hill Rd, Woodbury
$660,000
3 Beds ⋅ 3 Baths ⋅ 24125016 MLS
If you are looking for peace and tranquility, you will find it here in this expansive cape. Located on a quiet country road, it provides the privacy and tranquility as well as great spaces for a variety of lifestyles. For preparing great meals, this oversized kitchen is just the place. Enjoy friends and family as you prepare & dine. Spill over into the 25' x 22' family room with custom woodworking & a lovely fireplace. If you like to entertain in a more formal setting, use the spacious living & dining rooms. There is also a den/office on the main level. Upstairs, a primary bedroom suite as well as 2 additional bedrooms & an additional full bath. On the exterior, a spacious deck, patio a lovely yard as well as a spectacular 24' X 35' barn, great for entertaining, using as a workshop or as storage for special vehicles. The options are endless.

38 Barnhill Rd, Woodbury
$660,000
4 Beds ⋅ 3 Baths ⋅ 24010106 MLS
Come and enjoy this wonderful four bedroom home located within walking distance to Main Street through the field and down a little road to the post office, grocery store, community theater, schools, library, community center, antique shops and so much more. With the shortest of drives to Main Street enjoy the great restaurants, hiking trails, Hollow Park, Orenaug Park with a tower overlooking the town, outdoor and indoor concerts, playgrounds and sidewalks throughout Main Street. This home has hardwood throughout the first floor with a welcoming combined kitchen and family room with fireplace leading out through double doors to an 40' Trex deck and hot tub. The level screened back yard includes an Amish cottage style storage shed with electricity and beautiful flowering bushes lining the property line. See the list of attached upgrades . The heated carpeted basement room is ideal as a playroom, exercise or craft room. The owner has maintained and upgraded this home. It is truly move in ready! Located only 10 minutes to I-84, 30 minutes to the train and 1 1/2 hr by car to NYC. Readers Digest again named Woodbury the best small town in Connecticut and the Sunday New York Times featured Woodbury in the Living In section as Peace, Quaint Beauty and a Sense of History.

68 Sycamore Ave, Woodbury
$655,000
4 Beds ⋅ 2 Baths ⋅ 24027042 MLS
Don't sweat it! Just jump right in to your Gunite pool and relax by the pool in your private yard bordering open space. Fabulous expanded contemporary with wood floors, two fireplaces, oversized deck and three car garage. Gourmet kitchen with Wolf range with griddle and grill, Sub-zero frig and plenty of cabinetry. The Primary bedroom offers a wall of closets and spa-like bath with soaking tub. All bedrooms are spacious and one has a wall of bookshelves. The lower level family room has built-ins and a fireplace. House is equipped with a 22kw whole house generator. New front roof in June 2024. Town card lists 3 Bedrooms with office which can be used as 4th bedroom (1250 septic) The property is fully fenced and ready for new owners. Come take a look!

22 Forest Ridge Rd, Woodbury
$655,000
3 Beds ⋅ 3 Baths ⋅ 24029816 MLS
Welcome to 88 hard Hill Road in Woodbury, the charming family home you've been searching for! Located on a beautiful cul-de-sac with plenty of privacy, this 3 bedroom, 2.5 bath updated Colonial style home offers 2400 square feet of living space just minutes from the center of town. Nestled in the heart of Woodbury, renowned as the antique capital of Connecticut, this home provides a unique opportunity to enjoy a blend of historic charm and modern convenience. The desirable town of Woodbury boasts picturesque landscapes, a rich history, and a vibrant community, making it an ideal place to call home. This residence features an updated roof and siding complemented by Azek trim, ensuring sustained, hassle-free durability for years to come. Modern utilities include PEX plumbing, central heat and air conditioning, an underground propane tank, an on-demand water heater, an upgraded electrical panel, and an enhanced well system. A 20-kw automatic standby generator guarantees you'll never have to go without power. These upgrades ensure long-lasting efficiency and comfort, whether you're relaxing inside or enjoying the outdoors.

88 Hard Hill Rd, Woodbury
$650,000
3 Beds ⋅ 2 Baths ⋅ 24173939 MLS
Nestled on a picturesque 2+ acre park-like setting, this beautifully maintained 3-bedroom, 2-bath home offers the perfect blend of comfort, space, and natural beauty-with the ease of one-level living. Designed with both style and functionality in mind, the sun-filled open layout is enhanced by vaulted ceilings, skylights, and elegant bay windows, creating a bright and airy atmosphere throughout. The heart of the home features a chef's kitchen with a large island that flows seamlessly into the family room, with stone gas fireplace making it perfect for both everyday living and entertaining and adds warmth and character. A formal dining room and living room offer additional space for gatherings. The main level includes a spacious primary suite with a full bath, along with two additional bedrooms and a full hall bath. Enjoy peaceful mornings and relaxing evenings in the charming three-season room overlooking the private, scenic grounds, surrounded by nature and tranquility. The finished lower level provides exceptional additional living space, complete with a second stone fireplace-ideal for a recreation room, home office, or guest retreat. Plenty of storage in the walk-up attic with expansion possibilities. Set in a serene country setting yet just minutes from shopping, dining, and commuter routes, this home truly offers the best of both worlds.

207 Grassy Hill Rd, Woodbury
$650,000
3 Beds ⋅ 3 Baths ⋅ 24147278 MLS
Set on a picturesque lot with mature landscaping and gorgeous outdoor spaces, this beautifully maintained home offers a flexible layout designed for both entertaining and everyday living. The front entry opens to a bright and inviting living room with built-ins and gas fireplace. The kitchen blends style and function with granite countertops, stainless appliances, and a natural flow into the dining room that makes everyday gathering effortless. A glass door from the dining room leads to a stunning sunroom that connects directly to the two-car garage and provides access to the fenced backyard through both a standard door and a pet door. The living spaces are accompanied by a private primary suite with a walk-in closet and full bath, along with two guest bedrooms and a well-appointed full bath. Upstairs, a spacious family/rec room with a half bath creates a versatile retreat for play, relaxation, or visiting guests. The setting is exceptional. The rear of the property borders preserved parkland with woodland trails, while the land across the street is also protected, creating a tranquil backdrop and long-term privacy. Despite the peaceful surroundings, the home is only a short walk to Woodbury's town center, an uncommon blend of nature and convenience that is hard to replicate. With thoughtful updates, a flexible floor plan, and an outstanding location, 13 Park Lane offers a lifestyle that feels both connected and tucked away, an exceptional offering in the heart of Woodbury.

13 Park Ln, Woodbury
$650,000
5 Beds ⋅ 3 Baths ⋅ 24004748 MLS
Taking back-ups- Showcasing the splendor of its glory years in the heart of Woodbury's cherished Hotchkissville Historic District, this magnificent 1830 Greek Revival home - The Reuben J. Allen House - features a stunning, fully custom, hand-crafted master kitchen with a walk-in pantry, exquisitely restored original elements throughout the home, a full-floor master bedroom retreat with an en-suite bathroom and walk-in closet, four additional spacious bedrooms, abundant storage, bathrooms on every floor, a laundry room with custom cabinetry, a mud room, a large attached garage with a workbench and extensive shelving, a living room, parlor and dining room with two fireplaces perfectly suited for entertaining, and attention to artistic detail around every corner. Great care has also been taken to improve the infrastructure of the home, including the addition of all new plumbing, a new high-efficiency propane furnace, a new six-bedroom septic system (also a potential expansion opportunity), a new hot water tank, a new well, a new water softener and filtration system, all new appliances, including a 36-inch commercial gas range, all new siding, all new roofing, and new split-system heating and air conditioning in the master suite. In addition, the home's yard is expansive with flat open space for play, relaxing, and recreation. With Connecticut's famed Antiques Trail, shopping, parks, town library, community centers, and much more all within walking distance or a short drive.

240 Washington Rd, Woodbury
$649,900
3 Beds ⋅ 3 Baths ⋅ 24002472 MLS
Beautifully updated 3 Bedroom, 3 Bath Ranch on a fabulous lot with Westerly views! Inviting double doors lead you into the tiled entryway and an expansive sunken Living Room boasting a large fireplace with woodburning insert for cozy evenings and beamed cathedral ceiling. The generous and undated Eat-in Kitchen is open to the Dining Room and offers custom white cabinetry, Quartz counters, new appliances, an island and breakfast bar both w seating, large windows and easy access to the 2 car garage and yard. Down the hall you will find the Primary Bedroom Suite w large windows looking out on a lovely view, a walk-in closet, and attached full Bath. Two additional Bedrooms and a Hall Bath are also located in this area of the home. The Hall Bathroom has the laundry, 3 sinks and private bathing area. The nicely finished lower level offers a flexible floor plan w good ceiling height. A Family Room w wet bar, fireplace and walk out to the patio make this a great space for family entertaining. There are 3 additional rooms and a full bath located in the lower level along with a generous 5' high crawl space for all your storage needs. 2 enclosed porches are heated for additional space. The 2+ acre property boasts an inground Gunite pool with pool house and solar cover. Seller owned solar panels, generator switch, Renewal by Anderson windows in main level, Nest thermostats with zones, central vac, central air, new flooring throughout, updated electrical. Great location for commuters!

76 Hurds Hill Rd, Woodbury
$640,000
3 Beds ⋅ 3 Baths ⋅ 24114993 MLS
Falling water...Step away from the day and step on the property and take a deep breath. Instantly feel the weight of the worlds worries fade away. Commune with nature in this sanctuary property. From the front entry views direct to the back lush greenery, beautiful rock outcroppings and every window in between you can feel natures touch. Magnificent gardens and respite areas to sit and reflect or enjoy a book. Nature meets shelter. Open, inviting and warm spaces encompass you, step down from the foyer into the living room with cathedral ceilings, wood floors and a warming fireplace. Open to the dining room and then screened porch for cool spring and fall dining. Graciously inviting, custom designed, work and gathering space in the kitchen for laid back meal prepping and enjoying everyone's company. The den is a quiet retreat to work and enjoy the views from every window. Primary bedroom suite on the main level with vaulted ceilings, wonderful fireplace and natural light filled bath. Open balcony transfers the light and views thru to the upper two bedrooms that share a jack and jill bath. Expansive multi ground level decking, screened porch, beautiful native flowering shrubs and perennials everywhere you look. Brand new rf w transferable warranty (one small section is 10 yrs old). The Lower level is 3/4 finished, sliders out to the side decking, drop ceiling, walls, makes an amazing works space, or studio, needs flooring. Approx 1000 s/f of usable spac

32 Plumb Brook Rd, Woodbury
$635,000
4 Beds ⋅ 3 Baths ⋅ 24184647 MLS
Summer opportunity in a highly sought-after neighborhood featuring a private inground pool and backyard retreat. This one checks all the boxes-from cul-de-sac living to privacy and a great setting. Spacious 4-bedroom Colonial with hardwood floors, fireplace, and a partially finished walkout lower level. Sold strictly as-is and priced aggressively for a quick sale. Sellers have secured their next home and must move quickly. Needs very little to shine: strong bones, great location, and immediate equity potential. Opportunities like this don't last.

20 Stagecoach Rd, Woodbury
$635,000
4 Beds ⋅ 3 Baths ⋅ 170587660 MLS
Meticulously maintained home in a beautiful 1.67 acre landscaped setting. A stone walkway leads to the front door and porch where you can enjoy distant views. A spacious foyer greets you.The formal living room has French doors, a picture window, and walnut inlayed white oak floors.The large dining room has French doors, big picture window and a wood stove in the fireplace which can heat the entire home. The spacious eat-in kitchen offers plenty of cabinets, island, Viking stovetop, all new stainless appliances, granite countertops and the same walnut inlay on the white oak floors.Step into the large family room with vaulted ceilings and tons of light from the abundant windows, skylights and sliding doors.Doors lead to a stone patio with built-in stone seating around a gas or wood firepit.Rounding out the main floor is a completely renovated powder room with mosaic tiled accent wall.The upper level features the primary suite with a walk-in closet, additional closet and full en-suite bathroom with marble floors & countertop.The hall bathroom has marble floors, quartz countertop and double sinks.Three additional bedrooms complete the upper level. The lower level has plenty of room for storage and/or future finished space.The large deck stretching almost the entire back,offers space to enjoy the colorful sunsets.Stone walls dot the landscape.The wonderfully rich landscaping with private yard makes this a special place to relax in peace and tranquility of the open land and woods.

23 Hillside Rd, Woodbury
$632,500
4 Beds ⋅ 2 Baths ⋅ 24024876 MLS
Your search is over because this is the one you've been waiting for! This impeccably maintained, four-bedroom, oversized Cape-style home is privately set on an acre and a half of beautifully manicured grounds, complete with blue-stone walkways and fieldstone walls, on a secluded cul-de-sac road. The backyard oasis, featuring a stunning in-ground pool surrounded by a stamped concrete and Bluestone patio, as well as an upper-level wraparound Azek deck, makes this home the desired summer destination spot. No detail was spared on the interior, which boasts hardwood floors, custom millwork, and built-ins throughout. The main level features an open-concept kitchen with cherry cabinets, Corian countertops, stainless-steel appliances, a breakfast bar, and a separate breakfast area. The kitchen opens to a formal dining room and a large, cozy family room with wide-planked flooring, vaulted wood ceilings, skylights, and a blue-stone surround and hearth with a wood-burning stove. A formal living room with custom built-in bookshelves flanking a propane stove, two large bedrooms, and a remodeled full bathroom with tiled walls, granite countertop, and laundry complete the main level. The second level features a large primary bedroom suite with a French door leading to a magnificent custom-built walk-in closet and access to a remodeled full bath with a natural stone surround tub and shower. Additional storage and a generously sized second bedroom complete the upper level.

97 Hard Hill Rd, Woodbury
$629,000
4 Beds ⋅ 3 Baths ⋅ 24188362 MLS
Sited privately on 2.7 scenic acres in Woodbury's desirable Cardinal Hill neighborhood, this classic four-bedroom Colonial offers a perfect blend of quiet country living and everyday functionality. As part of a low-fee, self-managed neighborhood association, residents enjoy a wonderful sense of privacy and peace of mind. The main level features a traditional flow, including a formal living room and a separate dining room ideal for gatherings. Across the back of the home, a comfortable, open living space connects the eat-in kitchen-complete with a center island bar-to a cozy family room centered around a fireplace. This bright living area looks out to serene, elevated treetop views. A spacious pantry, dedicated laundry room, and a half bath complete the well-organized first floor. Upstairs, the primary bedroom suite features a private full bath and a spacious walk-in closet. Three additional bedrooms are nicely proportioned and share a full hallway bath. A traditional home in a peaceful, established setting just a short drive from the vibrant shops, eateries, and historic charm of downtown Woodbury.

18 South St, Woodbury
$629,000
3 Beds ⋅ 3 Baths ⋅ 24055622 MLS
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 mind. Originally a stagecoach stop, it stands near a brook that was once a favored path of the legendary Leatherman. In the 1970s, a visionary known as "Cadillac Joe" began expanding the home into a grand stone castle, meticulously crafting every stone by hand. Though his work was left incomplete due to his advancing age, the foundation he laid became the start of a stunning transformation. Enter Mario, whose dedication and years of hard work brought the vision to life, completing this architectural masterpiece with exceptional attention to detail. Today, "The Castle" stands as a beacon of history and craftsmanship, featuring a grand dining room, a massive living room, and a chef's kitchen-perfect for entertaining guests or simply enjoying the beauty of the space. The wraparound balconies offer breathtaking views over the river ravine and treetops, while the stone walkways and tranquil surroundings provide a peaceful retreat from the world. Whether you're captivated by the historic intrigue, the timeless craftsmanship, or the unparalleled setting, this home offers a truly unique living

514 Main St N, Woodbury
$628,500
2 Beds ⋅ 1 Baths ⋅ 24046164 MLS
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 innovative workshop. The property features a spacious garage and workshop area, each with impressive 17-foot ceilings and overhead garage doors. The workshop is equipped with a radiant heating system, ensuring a cozy and productive environment during the colder months. With zoning that supports owner-occupied businesses, this space is designed to adapt to your needs, whether for personal passion projects or professional endeavors. The single-family residence, provides a serene and private living area with stunning views of Three Rivers Park. The home includes a large, partially finished basement, offering potential for further expansion or customization. Please note that buyers interested in using the property for an owner-occupied business will need to secure approval from the Zoning Commission. This property is more than just a home; it's a haven for those who seek a harmonious blend of comfort and functionality. Contact us today to explore the endless possibilities this unique space offers. Agent is related to the owner.

49 Jacks Bridge Rd, Woodbury
$625,000
3 Beds ⋅ 2 Baths ⋅ 24170889 MLS
Timeless Elegance in the Heart of the Historic District . Step back in time without sacrificing modern convenience in this enchanting 1750s colonial, perfectly situated on a premier corner lot within the town's coveted Historic District. This home isn't just a place to live; it's a piece of local history loaded with "old world" character. From the moment you step inside, the rich wide plank hardwood floors and period details whisper stories of the past. The layout seamlessly blends cozy historic proportions with functional spaces designed for today's lifestyle. The kitchen features new cabinetry and appliances with adjoining stone floored sun room. Bright and airy rooms featuring original architectural charm. 2 well-appointed bedrooms offer peaceful retreats with a 3rd suitable as a nursery or office space. 1.5 baths include a convenient main-floor powder room. An expansive utility and mudroom provides ample storage and organizational space-a rare find in a home of this vintage. A lovely level corner lot is the perfect setting for this in town charmer. New 1250 gallon septic tank 2025. 24 hour notice for all showings please.

54 School St, Woodbury
$623,500
3 Beds ⋅ 4 Baths ⋅ 170589345 MLS
Welcome to this charming reproduction Cape Cod home in park-like setting! This timeless beauty is filled with character and boasts a wood roof and expansive front porch, providing a warm and inviting exterior. Step inside and be captivated by the elegant brick accents and wide board pegged hardwood floors, exuding a classic yet sophisticated atmosphere. With not one, not two, but three fireplaces, you'll enjoy cozy evenings and a touch of romance throughout the house. The first floor features a delightful surprise.. a primary bedroom suite offering convenience and flexibility for your lifestyle. In addition to its charm, this home has been thoughtfully updated, ensuring modern comforts without compromising its traditional allure. The layout even allows for a potential in-law setup if needed, making it ideal for multi-generational living or welcoming guests. Don't miss your chance to own this enchanting Cape Cod reproduction, a home that harmoniously blends old-world charm with contemporary living. New whole house generator for added peace of mind. Schedule a showing today and experience its captivating beauty for yourself!

591 Upper Grassy Hill, Woodbury
$622,500
4 Beds ⋅ 2 Baths ⋅ 24000228 MLS
This Greek Revival home in the heart of Woodbury's Historic District was built in 1829 as illustrated and described in Old Homes of Woodbury. It maintains original details and includes a breakfast room next to the kitchen 16x13. The charm throughout the home with its wide board floors, plenty of windows and light, Belgian Block courtyard together with its cozy side porch makes this a wonderful place to live. Enjoy the perennial plantings, vegetable and herb gardens plus a 3 season porch on the second floor. The two story oversized barn was once an antique shop and parking for at least two cars is convenient. The present owner has supplied a list of upgrades which illustrate the love they have for this home. In the Living In Sunday section of the New York Times dated may, 2021 it features Woodbury, Ct as Peace, Quaint Beauty and a Sense of History. The Reader's Digest again just called Woodbury "The Best Small Town in Ct." This convenient location makes walking a pleasure to stores, library, community center, schools, medical appointments, summer outdoor concerts, community theater, beautiful live music in Hollow Park plus hike to the tower overlooking the town and so much more! Come and enjoy this home and the wonderful small town with parks and open space, Flanders Nature Center, hiking trails, its roads meandering past three rivers--the Pomperaug, Weekeepeemee and Nonnewaug plus golf courses and private schools nearby.

60 Main St S, Woodbury
$615,000
3 Beds ⋅ 3 Baths ⋅ 24099745 MLS
Majestically perched on 2+ private acres, this beautifully maintained three-bedroom Colonial offers seasonal panoramic views of rolling hills and treetops, providing a picturesque year-round backdrop while being close to town. Thoughtfully updated with modern finishes, this home blends comfort and style with ease. Step into the inviting Great Room, where soaring ceilings with exposed beams, expansive windows, and a sliding door to the back deck create a bright, open atmosphere. The Eat-In Kitchen, seamlessly connected to the Great Room, features high-end finishes, GE Profile appliances, and ample cabinet space-perfect for entertaining. Enjoy hosting in the spacious Dining Room or relaxing in the formal Living Room. A convenient mudroom area with laundry and a half bath offers its own entry from the deck. Upstairs, you'll find three freshly carpeted bedrooms and two full baths, including a Primary Bath with heated floors for added comfort. The floored attic includes a separate storage room and offers potential for future expansion. This exceptional property is a must-see. Schedule your tour today!

130 Grassy Hill Rd, Woodbury
$612,500
3 Beds ⋅ 2 Baths ⋅ 24177873 MLS
Fantastic Potential in this home. Three bedroom Cape Cod sitting on 5.50 acre lot with a giant barn that has great potential living space to convert into an in-laws set up, office, studio space or music studio to fit your lifestyle. Home freshly painted interior and exterior. Renovated kitchen with all new countertops and Italian farmhouse sink, floors, Pantry, refreshed cabinets. All newer energy star appliances. Updated bathrooms- new vanities, tile, floor, and walk-in shower in upstairs bath. Walk out into your large screened in porch to enjoy the beautiful quiet and nature surrounding you in your lovely home. Giving you a peaceful retreat. New roof 2022. New heat pump hot water heater 2022 . New water holding tank 2025. Mini Splits installed in 2020. Entire house water filtration system. New cast iron woodstove installed in 2021 with refaced fireplace. Lots of space to run and play. Private hiking and biking trails with a campsite at the top of the property complete with fire pit. Grow a Beautiful garden of vegetables, with pretty flowers and flowering trees surrounding you. The lot is large enough for poultry or livestock for those of you with Love of animals? The two car garage has electric car outlet. 9.8 kW Solar array installed 2020.Seller owned Solar panels on the property for those energy saving consumers. So much potential, so much to see, schedule your tour soon!

16 Cross Brook Rd, Woodbury
$610,000
4 Beds ⋅ 3 Baths ⋅ 24046797 MLS
WELCOME! This private and well-maintained colonial farmhouse is nestled on 4.8 serene acres, ideal for accommodating family and guests, or as a tranquil getaway home containing 3416 total s.f. The Kitchen features granite countertops, gas range and custom tile backsplash. The adjoining great room w/ wood-burning fireplace, stone mantle, vaulted ceiling and exposed beams is perfect for gatherings or a quiet night in. A bright dining room and large sun-filled living room finish the main level, along with a full bath and convenient laundry room, gleaming hardwood floors throughout. A delightful 3-season sunroom with adjacent deck overlooks the backyard. The upper floor features a generous primary bedroom with walk-in closet and en-suite bathroom. 3 additional bedrooms and full bath allow for guests, or additional office or creative space. The finished 900 s.f. lower level boasts new flooring, recessed lighting and charming wood-burning stove to provide additional living space options, including separate access. New exterior paint and siding (2024), new furnace (2022), new HVAC, new well pump, new roof (2022 and 2011). 1st owner was builder, 2nd owner is the Seller. Abuts open space. Just minutes to Woodbury's quintessential New England town center or to Southbury's commercial center. Easy access to I-84, 90 min. to NYC, and 35 min. to Metro-North at Southeast.

652 Upper Grassy Hill, Woodbury
$605,000
3 Beds ⋅ 4 Baths ⋅ 24183597 MLS
Charming in-town Gambrel Colonial with views of Orenaug Pond, located just up the road from the South Green. Surrounded by historic landmarks such as King Solomon's Lodge, the Hurd House, the Glebe House, and other notable properties, this home offers three bedrooms, three full baths, and one half bath. It also features a remodeled kitchen with stainless appliances that opens to a family room with vaulted ceilings. Additional highlights include a partially finished walk-out basement, an attached two-car garage, an oversized deck, and private yard. Close to parks, private schools, tennis and swim clubs, shopping and more. Come fall in love with Woodbury.

30 Park Rd, Woodbury
$600,000
4 Beds ⋅ 3 Baths ⋅ 24191268 MLS
Have you been looking for a Woodbury home with that special balance of privacy and accessibility? This well-maintained four bedroom, three bath Colonial may just be the answer. The heart of the home is a bright, sunlit kitchen and breakfast nook that opens into a spacious family room with a wood-burning brick fireplace and skylights in a vaulted ceiling; sliders lead to a large 32 x 16 foot deck overlooking the level back yard. A formal living room offers additional space for entertaining and holidays are a breeze thanks to a formal dining room, with all the rooms flowing easily from one to the next. The primary bedroom suite with three additional bedrooms on the upper level feature hardwood floors (one bedroom has hardwood under the carpet) and both smartly updated baths look fresh and inviting. There's easy access to the attic through a guest bedroom closet. The partially finished lower level offers more flexible space and is where you find the laundry and mechanical rooms as well as access to the two-car garage. Gardeners will appreciate the greenhouse, and the spacious yard offers nearly limitless options for those with a green thumb. Lovingly cared for by one owner for the past forty years, you will not be disappointed when you see this wonderful property. Come home to Woodbury, the gateway to extraordinary Litchfield County.

38 Grey Fox Trl, Woodbury
$600,000
3 Beds ⋅ 3 Baths ⋅ 24039694 MLS
Located in a quiet corner of Woodbury is this lovely 1930's colonial on 1.84 acres. Delightful details include the arched doorways in the main foyer, stone fireplace in the living room, oak floors throughout and French doors here and there. The kitchen and two and half bathrooms have been updated and the exterior has recently received a fresh coat of paint. The main level includes the living room, formal dining room, kitchen, mudroom and an extra room to use as a family room, study or office with 3 walls of windows. Upstairs is the primary bedroom with full bath, two other bedrooms, hall bath and laundry room. The grounds are spectacular with an abundance of lush, lawn, beautiful trees and detached two bay garage. There is hydro air heating and central air conditioning. Property sits back from the shared driveway that leads up to Four Winds Farm, a private equestrian property. Come take a look!

233 Old Sherman Hill Rd, Woodbury
$600,000
3 Beds ⋅ 3 Baths ⋅ 24046120 MLS
Beautifully renovated and remodeled split-level in convenient location . All new interior and exterior, mechanicals, insulation, gutters - from soup to nuts! The Great room is the heart of the home and encompasses the living room, gorgeous kitchen and dining area. The living space has a fireplace, wood floors and picture window with view of large level front yard. The brand new modern kitchen has stainless steel appliances, granite countertops, island with breakfast bar and sliders to rear deck. A few steps up brings you to the primary bedroom with remodeled full bath, wood floor, two closets and ceiling fan. There are two bedrooms with wood floors, ceiling fans and double closets that share the second full remodeled bath in the hall. A few steps down from the main level is the spacious family room and office with sliders that lead to the two bay carport and detached one bay garage. Also on this level is a half bath and laundry room. Efficient Hydro air heating system and central air conditioning. The house sits back off the road. Woodbury is designated as Connecticut's "Most charming small town," by Reader's Digest and boasts tree-lined Main St, parks, playgrounds, hiking trails and streams. Known as the "Antiques capital of CT," there's no shortage of shops, boutiques and antique homes lining historic Main St.

23 North Rd, Woodbury

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.