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$329,900
3 Beds ⋅ 2 Baths ⋅ 24195376 MLS ⋅ Woodbury Place BLDG.
Move right into this beautifully updated 3-bedroom, 2-bath townhouse offering style, comfort, and low-maintenance living. Gleaming hardwood floors flow throughout the home, complemented by vaulted ceilings, a skylight providing abundant natural light. The updated galley kitchen features tasteful tile backsplash and efficient design, opening to a spacious living and dining area highlighted by a cozy electric fireplace and ceiling fan. Sliding glass doors lead to a private patio with peaceful ideal setting for morning coffee, birdwatching, entertaining or simply relaxing. A convenient outdoor storage shed adds extra functionality. The main level offers two generously sized bedrooms with ample closet space, a full bath a including washer and dryer closet. Upstairs, a dramatic open loft overlooks the living area and leads to a spacious primary suite featuring a unique barn-door closet, walk-in closet, and an updated full custom tiled shower with double vanity, skylight and elegant cabinetry. Wake up to seasonal lake views from the primary bedroom suite. Central Air & updated blown in insulation are just some additional perks. A detached two-car garage provides additional storage and convenience along with an additional dedicated parking space. Ideally located with easy access to I-84, charming shops, a plethora of dining and so much that Southbury and Woodbury have to offer. This exceptional home combines comfort, convenience, and scenic surroundings in desirable Woodbury Place.

22 Woodbury Pl Unit 22, Woodbury
$1,395,000
3 Beds ⋅ 3 Baths ⋅ 24192284 MLS
Steeped in 18th-century charm, this rare 1747 Saltbox estate seamlessly marries historic integrity with modern luxury. Tucked away on a peaceful country lane, the main home boasts original wide-plank wood floors, dual fireplaces, twin staircases, authentic built-ins, and freshly renovated baths. At its heart is the kitchen featuring Viking appliances and granite counters that open to garden views. Step through the screened stone-and-timber breezeway to a newly expanded patio and custom firepit crafted directly from native fieldstone, all beneath a classic wood-shingle and copper roof. The surrounding grounds function as a true New England compound. A separate two-bedroom carriage house offers built-in guest quarters with a covered porch and an oversized 2.5-car garage. Nearby, a newer two-story 40'x28' barn provides flexible space for a creative studio, vehicle storage, or livestock, complemented by two additional storage sheds. Recent improvements include, but are not limited to, a new cedar-shingle roof with copper downspouts (2025), new A/C, fresh interior paint throughout (2026), and refinished flooring. It is an unmistakable rural sanctuary with abundant room for hosting friends and extended family.

509 Weekeepeemee Rd, 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
$819,900
3 Beds ⋅ 3 Baths ⋅ 24192675 MLS
Welcome to 17 Curtiss Road! This one-of-a-kind 1.8-acre property offers the perfect blend of historic charm and modern convenience, featuring a well-maintained 1900 single-family home, an attached 2-car garage, and an impressive detached 24' x 50' heated 3-car garage built in 2022. Step inside the home and be welcomed by a charming foyer leading to wide-board hardwood floors and six mini-split systems (2019) that provide efficient heating and cooling throughout. The inviting living room features custom built-ins and flows seamlessly into the spacious kitchen, complete with stainless steel appliances, ample cabinetry, recessed lighting, a pantry closet, and basement access. Just off the kitchen is an updated half bath with tile flooring and laundry hookups. Off the kitchen the elegant dining room offers crown molding and plenty of space for entertaining. Completing the main level is a spacious primary suite with double closets and a beautifully updated full bath boasting heated tile floors, a skylight, recessed lighting, chair rail molding, and a linen closet. An adjoining den with custom built-ins provides the perfect space for a home office, reading room, etc. Upstairs, you'll find two generously sized bedrooms, each with walk-in closets and shared access to a Jack-and-Jill bathroom featuring a dual-sink marble vanity. The basement includes 200-amp electrical service, Energy Star hot water heater, well tank (2018), and additional laundry hookups. Outside, enjoy

17 Curtiss Rd, Woodbury
$349,500
3 Beds ⋅ 3 Baths ⋅ 24191489 MLS ⋅ Woodlake BLDG.
Welcome to Woodlake! Move right in and enjoy the space, comfort, and lifestyle this beautifully maintained 3-bedroom, 2.5-bath townhouse has to offer. The light-filled and flexible floor plan includes spacious main-level living, 2 generous upstairs bedrooms, and a huge finished walkout lower level with an additional room perfect for a home office, gym, or hobby space. Updates and improvements are too numerous to mention. Highlights include an electric fireplace insert, a cozy wood stove, and a beautifully renovated upstairs bath with a jetted tub. (Ask your Realtor for a full list.) A large unfinished basement area provides abundant storage. Outside, enjoy a meal or coffee on your private deck, and you'll even enjoy the short scenic walk from your car (1 carport and 1 assigned parking spot!) to your front door. Life at Woodlake is about more than the home. Enjoy walking trails, a tranquil pond for canoeing, picnic areas, a playground, and a peaceful setting surrounded by nature. Just minutes away, historic Woodbury offers exceptional restaurants, charming shops, antique stores, New Morning Market, Flanders Nature Center, Earth Tones Native Plant Nursery, and easy access to I-84, giving you the perfect blend of country charm and everyday convenience. As an added bonus, Woodlake is FHA-approved and pet-friendly. Schedule your private showing today and experience everything Woodlake has to offer.

4 Alder Court, Unit 4, Woodbury
$398,000
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
$525,000
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
$250,000
24192651 MLS
An exceptional opportunity to own 76.9 +/- acres in one of Woodbury's most desirable locations. This unique offering includes two contiguous parcels to be sold together, consisting of this 14.9-acre parcel and the adjoining 62-acre parcel (MLS #24192209). Featuring a charming 3-bedroom home, the property offers a rare combination of rolling meadows, mature woodlands, and open fields, creating endless possibilities for the next owner. Whether you're seeking a private country estate, equestrian property, family compound, recreational retreat, hunting property, or a prime development opportunity, this expansive acreage provides the flexibility to bring your vision to life. Surrounded by the natural beauty of Woodbury while offering convenient access to local amenities, this is a truly remarkable opportunity to invest in one of Litchfield County's most sought-after communities. A rare offering where privacy, scenic landscapes, and future potential come together.

Hoop Pole Hill, Woodbury
$1,000,000
24192209 MLS
An exceptional opportunity to own 76.9 acres in one of Woodbury's most desirable locations. This unique offering includes two contiguous parcels to be sold together, consisting of 14.9-acre parcel (MLS# 24192651) and this adjoining 62-acre parcel Featuring a charming 3-bedroom home, the property offers a rare combination of rolling meadows, mature woodlands, and open fields, creating endless possibilities for the next owner. Whether you're seeking a private country estate, equestrian property, family compound, recreational retreat, hunting property, or a prime development opportunity, this expansive acreage provides the flexibility to bring your vision to life. Surrounded by the natural beauty of Woodbury while offering convenient access to local amenities, this is a truly remarkable opportunity to invest in one of Litchfield County's most sought-after communities. A rare offering where privacy, scenic landscapes, and future potential come together.

245 Hoop Pole Hill Rd, Woodbury
$1,100,000
4 Beds ⋅ 4 Baths ⋅ 24192457 MLS
Spacious Colonial in desirable Carriage Hills offers approximately 5,700 square feet of living space, including a walk-out lower level that is well suited for an in-law suite or au pair quarters. The main level features wood floors, formal living and dining rooms, an eat-in kitchen, a bedroom, a full bath, and a family room with a fireplace that opens to an oversized deck. Upstairs, you'll find three bedrooms, a full bath, and a spacious primary suite with a spa-like bath and loft area. The walk-out lower level includes three finished rooms plus a full bath, offering flexible space for guests, extended living, recreation, or work-from-home needs. The private backyard is surrounded by trees and accented with perennial gardens. NEW Roof June 2026. Located in Woodbury-one of Connecticut's most beloved small towns-the home is close to charming shops, antique stores, coffee shops, and restaurants, all just about 90 minutes from New York City.

16 Gate Post Ln, Woodbury
$675,000
4 Beds ⋅ 3 Baths ⋅ 24192145 MLS
Exceptional opportunity to renovate and create your dream country estate on 12.69 private acres in the heart of Woodbury. Privately sited along a quiet country road with seasonal long views, this 2,972 sq. ft. contemporary offers an outstanding combination of acreage, privacy, and potential rarely found at this price point. Designed for comfortable living, the home features a dramatic sunken living room with soaring vaulted ceilings, a fireplace, and walls of windows overlooking the surrounding landscape. The main level includes a spacious primary suite, private office, butler's pantry, and access to expansive decks that invite outdoor entertaining. Upstairs are 3 additional bedrooms and an open den, while the unfinished walk-out lower level offers endless possibilities for future living space. The property's 12.69 acres provide a beautiful backdrop with open land, mature trees, and a four-stall barn, offering flexibility for a variety of country lifestyles. Priced to reflect the opportunity for renovation and updating, this is an exceptional chance for investors, builders, or buyers looking to customize a solidly built home in one of Woodbury's most desirable locations. With great bones, an outstanding setting, and significant upside potential, this property is ready for its next chapter. Sold as is.

348 Hoop Pole Hill Rd, Woodbury
$749,900
3 Beds ⋅ 3 Baths ⋅ 24190540 MLS
Charming and full of character, this beautifully maintained three-bedroom Cape offers the perfect blend of comfort, warmth, and convenience in the heart of Woodbury. Set on a picturesque property with mature perennial gardens and a fenced-in yard, the home feels peaceful and private while being just a two-minute walk from downtown shops, restaurants, the library, schools, community center, and nearby hiking trails. Inside, hardwood floors and abundant natural light create a warm and inviting atmosphere. The welcoming living room features a fireplace, while the bright south-facing sunroom provides a relaxing space to enjoy throughout the day. The dining room includes a charming corner cupboard that adds timeless New England character. The finished lower level offers flexible space for exercise, hobbies, or creative pursuits and includes a sauna, shower, and fully equipped darkroom. Additional highlights include a two-car garage and beautifully landscaped outdoor spaces. A rare opportunity to enjoy distinctive features, exceptional charm, and an ideal in-town location in one of Litchfield County's most desirable communities.

31 Mountain Rd, Woodbury
$579,000
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
$179,900
2 Beds ⋅ 1 Baths ⋅ 24190522 MLS ⋅ Town In Country BLDG.
Welcome to Town In Country, a sought-after condominium community conveniently located just minutes from the heart of Woodbury. This 2-bedroom, 1-bath lower-level ranch-style unit offers comfortable one-level living with an open layout and abundant natural light. Laminate flooring runs throughout the living areas and bedrooms, while the kitchen and bathroom feature durable tile flooring. The bathroom includes an attractive vanity and additional storage. Enjoy the convenience of walkout access and a private patio area overlooking the beautifully maintained grounds, along with assigned parking and low-maintenance living. Residents enjoy access to an in-ground pool, picnic areas, and professionally maintained common grounds, all while being close to Woodbury's charming Main Street, local shops, restaurants, parks, and everyday amenities. With easy access to Routes 6 and 64, this is an excellent opportunity for a first-time buyer, downsizer, or anyone seeking affordable homeownership in one of Litchfield County's most desirable towns.

229 Bacon Pond Rd Unit 452, Woodbury
$258,000
2 Beds ⋅ 2 Baths ⋅ 24190618 MLS ⋅ Woodlake BLDG.
Welcome home to this sun-filled end unit nestled in the highly desirable Woodlake condo community. Offering a perfect blend of comfort, style, and privacy, this beautiful property features nearly 1,200 square feet of thoughtfully designed living space. Step inside to find an inviting, spacious layout seamlessly connecting the main living areas, featuring 2 generously sized bedrooms and 2 full bathrooms. The heart of the home boasts a pristine kitchen complete with beautifully updated cabinetry, providing ample storage, modern flair, and plenty of counter space for the home chef. Peace of mind comes easy with a brand-new Central AC system installed, ensuring maximum energy efficiency and crisp, cool comfort all summer long. The bright interior flows effortlessly out to your own expansive private back deck, an ideal outdoor oasis for morning coffee, weekend barbecues, or simply unwinding in the evening while enjoying the extra quiet and serene, park-like views that come with a premium end-unit location. Adding to the long list of features is the incredible convenience of a detached garage, keeping your vehicle protected from the elements and offering excellent additional storage space. Combining a spacious floor plan, mechanical upgrades, and a tranquil wooded setting, this turnkey home delivers low-maintenance Connecticut condo living at its absolute finest.

10 Summit Court Unit 10, Woodbury
$185,000
2 Beds ⋅ 1 Baths ⋅ 24189883 MLS ⋅ Town In Country BLDG.
Welcome to this highly sought after and rarely available upper end unit in Woodbury's charming and serene Town in Country condominium complex. This updated unit boasts a renovated kitchen and newer floors throughout the well-designed layout. The open concept kitchen, dining, and living room is perfect for everyday living and entertaining guests. Step through the slider doors onto a large balcony deck with views of the surrounding greenery and woods. Two generously sized bedrooms and a full bathroom wrap up this light-filled and spacious end unit. Enjoy the in-ground pool and picnic area just a short walk away. This is one of Woodbury's most affordable communities to own in. Don't hesitate to take this opportunity and make this unit yours!

229 Bacon Pond Rd Unit 354, Woodbury
$895,000
4 Beds ⋅ 3 Baths ⋅ 24172964 MLS
QUAIL RUN On the cul de sac - 4 NEW HOMES ALL ON FLAT LOTS! They might be what you have been looking for - SMALLER & SMARTER new homes with PRICES TO MATCH. Beautiful 1 acre+ lots on shared common drives surrounded by 12 ACRES OF PRIVATE OPEN SPACE. This is QUINTESSENTIAL WOODBURY - Quiet, woodsy, and BEAUTIFUL! 2 homes IN CONTRACT, 1 home available for FALL DELIVERY and this new build to start in later summer/early fall for SPRING DELIVERY 2027.

96 Quail Run Rd, Woodbury
$220,000
2 Beds ⋅ 1 Baths ⋅ 24190026 MLS ⋅ Town In Country BLDG.
Welcome to 229 Bacon Pond Rd Unit 312 - located in the Town In Country complex, this 2 bed/1 bath unit has been remodeled from top to bottom featuring a brand new kitchen, new flooring, and central air. Inside you'll find an open floor plan perfect for entertaining - the kitchen has been completely redesigned featuring new cabinets, quartz countertops, and stainless steel appliances. The modern flooring flows from the kitchen to the fireplace, offering a perfect place for family gatherings. Around the corner you'll find two bedrooms and 1 full bath - the bathroom has been updated and modernized featuring a brand new vanity and tiled shower. The slider door leads to a private patio which is just a short walk down to the in ground pool. Enjoy everything Woodbury has to offer - Rt. 6 is minutes away offering plenty of restaurants and shopping, with I84 just a short drive away. Whether you enjoy laying by the pool or hiking through a number of trails this is the perfect location for the discerning consumer.

229 Bacon Pond Rd Unit 312, Woodbury
$495,000
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
$575,000
3 Beds ⋅ 3 Baths ⋅ 24185429 MLS
Cute as a button Cape Cod style home in charming and historic Woodbury! A lovingly cared for home within a short drive of main street, area schools, Walker Road Winery and all other major conveniences. Step right into this light and bright home that provides a newly remodeled kitchen, oak floors throughout, two bedrooms on the main level and charming exposed beams. Comfortable and cozy, sit and relax in the living room that is just off the kitchen, and end your day in the first floor primary suite that includes two walk-in closets with bath including a newer vanity and stall shower. Rounding off the main level is another full bath. Upstairs find two additional bedrooms and full bath. Several recent upgrades include a newer roof, gutters, and siding. The two bay attached garage features workshop, 100amp sub panel, and loft area for additional storage or conversion into an in-law apartment with connection to the septic system already! Still need more space for storing your equipment and toys? Included on this property are two outbuildings, one is 12x20, the other is 18x33. Town records show 3 bedrooms, septic was replaced as 4 bedroom. Bring your hobbies and make this charming Cape yours today!

206 Minortown Rd, Woodbury
$229,000
2 Beds ⋅ 2 Baths ⋅ 24188657 MLS ⋅ Woodlake BLDG.
Escape to the feel of a Vermont ski chalet-without leaving Connecticut! This spacious townhome features an open, airy floor plan that's full of potential and just waiting for your personal touch. The flexible main level adapts to your lifestyle, with a sunny breakfast/dining area off the kitchen that also works beautifully as a home office, playroom, or could even be converted into a convenient first-floor bath with laundry. The oversized living room opens to a private deck overlooking a peaceful green lawn and distant woods- the perfect spot for morning coffee or unwinding at the end of the day. The fireplace is currently capped, but with permits can be brought back to life and fitted with a pellet or wood-burning stove insert. Upstairs, you'll find two generously sized bedrooms, including a private primary suite, both with double closets, plus a second full bath. The heated lower level offers endless possibilities-create a family room, home gym, hobby space, or guest retreat. Life at Woodlake feels like a year-round vacation with a scenic pond for paddle boating, tennis courts, hiking trails, a playground, picnic area, and the community's iconic gazebo. Just minutes away, charming Woodbury offers acclaimed restaurants, one-of-a-kind boutiques, and is proudly known as Connecticut's Antique Capital. Enjoy peaceful country living while remaining close to I-84 and everyday shopping conveniences!

16 Fox Run, Unit 16, Woodbury
$310,000
2 Beds ⋅ 3 Baths ⋅ 24188916 MLS ⋅ Woodlake BLDG.
Nestled in a serene setting backing up to peaceful woods, this beautifully updated tri-level townhouse offers the perfect blend of comfort, style, and privacy. Freshly painted throughout, this spacious home features 2 bedrooms, 2.5 bathrooms, and a finished basement, providing plenty of room for living, working, and entertaining. The open-concept layout is filled with natural light and includes a cozy fireplace that creates a warm and inviting atmosphere. Step outside to your private patio, where you can relax and enjoy the tranquil wooded backdrop. With modern updates, generous living spaces, and a desirable natural setting, this move-in-ready townhouse is a wonderful place to call home.

11 Lower Commons, Unit 11, Woodbury
$395,000
24187054 MLS
Nestled along one of Woodbury's finest country roads, this exceptional 2.53-acre parcel offers a rare masterclass in privacy and natural beauty. Located just moments from the Roxbury town line, the gently rolling landscape is framed by mature trees and directly abuts the Arthur Miller Preserve and the Frank and Ellen McCort protected Land Trust. Positioned just two homes away from the historic Calder Estate, the setting creates an extraordinary sense of quietude and absolute seclusion. The property features a magnificent all-season running stream with its own natural waterfall, dramatically enhancing the native wildlife and scenic beauty of the area. Enveloped by the timeless allure of Litchfield County, this land offers an ideal canvas for an architectural masterpiece, a private weekend retreat, or a magnificent legacy estate. Its pristine setting, open spaces, and dramatic yet intimate feel provide the perfect balance of country elegance and everyday livability. Peerless privacy, a coveted location, protected surroundings, and an immediate neighborhood of significant homes make this a compelling opportunity in one of Connecticut's most desirable country settings-just minutes from the refined charm of Roxbury and Washington, and approximately 90 minutes from NYC.

133 Painter Hill Rd, Woodbury
$799,900
4 Beds ⋅ 3 Baths ⋅ 24185801 MLS
Beautifully renovated 4-bedroom, 2.5-bath ranch set on a spacious corner lot in one of Woodbury's most desirable locations. Just two streets from Woodbury's nationally recognized Main Street, this home offers the perfect combination of modern updates, comfortable living, and exceptional outdoor entertaining. The complete interior renovation began in 2023 and has recently been completed, creating a truly move-in-ready home. At the heart of the property is a stunning open-concept kitchen featuring stylish finishes and thoughtful design, seamlessly flowing into the dining area and living room-ideal for both everyday living and hosting family and friends. The private primary suite offers beautiful views of the backyard retreat, while three additional generously sized bedrooms and a fully renovated full bathroom provide plenty of space for family and guests. Every bathroom in the home has been tastefully updated, complementing the home's fresh, modern feel. Step outside to your own backyard oasis. The expansive outdoor space features a large in-ground swimming pool, dedicated BBQ area, and ample lawn space for entertaining, yard games, and summer gatherings. Whether you're hosting a crowd or enjoying a quiet evening at home, this outdoor setting is sure to impress. Adding even more versatility is the separate pool house, complete with accommodations that offer endless possibilities for guests, extended family, a home office, or private retreat.

62 Heritage Dr, Woodbury
$449,000
3 Beds ⋅ 3 Baths ⋅ 24099709 MLS
Nestled in the highly desirable town of Woodbury, this charming Cape offers just over 2,000 square feet of comfortable living space with endless potential. The home features 3 bedrooms, 2.5 bathrooms, and beautiful hardwood floors throughout. A dedicated home office with custom built-in shelving provides the perfect space for working from home or studying. The inviting living room includes a cozy pellet stove, creating the perfect gathering space. The bright dining room features a large picture window that fills the space with natural light. A spacious mudroom with vaulted ceilings, laundry hookups, and a large walk-in pantry provides exceptional everyday convenience. Step outside to enjoy the 1.5 acre private setting, complete with an in-ground pool and safety fence-ideal for relaxing, entertaining, or making the most of New England summers. Whether you're looking to restore its original charm or add your own personal touches, this home presents an excellent opportunity to build equity in one of Litchfield County's most sought-after communities. New windows, siding and gutters in 2024. The property is being sold "as is." Don't miss your chance to make this Woodbury property your own!

241 Hoop Pole Hill Rd, Woodbury
$1,795,000
2 Beds ⋅ 2 Baths ⋅ 24185479 MLS ⋅ Woodlake BLDG.
Just 2 hours from New York City, this exceptional lakefront retreat offers a rare blend of privacy, natural beauty & turnkey luxury. Tucked at the end of West Lake Rd and bordered by the protected woodlands of Flanders Nature Center Preserve, the property enjoys sweeping, unobstructed views across pristine Lake Quassapaug to historic Tranquillity Farm, designed by McKim, Mead & White. Lake Quassapaug is a private lake with no public access & a 10-mph speed limit, creating an ideal setting for boating, fishing, swimming & year-round recreation. Private beach & dock provide direct water access, while the renovated lakeside cabana offers flexible space for a home office, fitness studio or retreat. Outdoor KIT, BBQ area & multiple patios, including a waterfront terrace, are perfect for entertaining. Renovated in 2020, the home features a beautifully appointed gourmet KIT with premium finishes & seamless flow to inviting living spaces. One of only a select few lakefront homes in Woodbury, it benefits from the town's favorable tax structure while being minutes to historic Main St, acclaimed restaurants & antique shops. Town of Woodbury recognizes 112 West Lake Road and a few other neighboring properties as condominium units. All other homes on the Lake are in Middlebury CT. Rare opportunity to own a fully renovated waterfront home with exceptional privacy, spectacular views & an unparalleled lake lifestyle.

112 W Lake Rd Unit 112, Woodbury
$1,790,000
4 Beds ⋅ 3 Baths ⋅ 24184948 MLS
It's rare to find a vintage estate tucked away from a main road, but this one sits at the end of a private lane, opening to 6.3 enchanting acres framed by stone walls, manicured gardens, and a charming vintage home. The property includes a large custom two-story pole barn, inground pool, detached three-bay garage, and an adorable potting shed. The great room flows into a kitchen with handmade cabinetry, butler's pantry, soapstone counters, and a Vulcan stove, all centered around a brick fireplace flanked by double French doors leading to a shady brick patio. Off the kitchen, a spacious screened porch surrounded with stone walls, offers a peaceful spot to enjoy the seasons. The formal living room, currently an office, boasts a light-filled five-window bay, while two front entry rooms serve as a den and library. The primary suite, in its own wing above the great room, features a private living room, full bath, sleeping area, and views of Perkins Ponds. Three additional bedrooms, accessed via a second staircase, are bright, charming, and surprisingly well-appointed with closets. The impressive barn offers tandem bays for vehicles, a heated workshop, and two upper rooms perfect for future studio spaces. Relax by the pool, take in the flowers, and enjoy the chorus of birds.

40 Ruffin Rd, Woodbury
$849,000
3 Beds ⋅ 2 Baths ⋅ 24182784 MLS
Live Stress-Free in This Income-Producing Equestrian Retreat! Enjoy the best of country living while generating income from your property. Rental revenue from a separate 1 BR apartment and 4 of the 10 horse stalls offers a rare opportunity to offset ownership costs! Situated on 5.76 level acres of open pasture and riding space, this equestrian property is ideal for horse enthusiasts, trainers, or anyone seeking a peaceful rural lifestyle. The horse facilities include 4 barns with a total of 10 stalls, 2 wash stalls, and a 20 x 60-meter riding arena with premium stone dust and sand footing. The grounds offer ample space for turnout, training, recreation, and relaxation, creating the perfect balance of functionality and tranquility. At the heart of the property is a charming 3-bedroom, 2-bath ranch home featuring a windowed kitchen, spacious dining room for entertaining, vaulted ceilings, 2 fireplaces with wood stoves, a WIC, and an oversized lower-level bonus room. Step outside to a private backyard designed for gatherings and enjoyment, complete with a thriving vegetable garden. The 1 BR apartment is currently rented, but can easily serve as an in-law suite or guest quarters. There is also a 3 car garage for the car enthusiast! The possibilities are endless! The present owners, Serenity Farm Horse Rescue, have lovingly cared for this property for years. As their rescue continues to grow, they are seeking a larger facility to support their expansion. Shown by private appt.

92 Minortown Rd, Woodbury
$865,000
4 Beds ⋅ 2 Baths ⋅ 24183601 MLS
Built in 1854, this 5.91 acre property offers an incredible value impossible to replicate today for the price. The property includes an Italianate stone home with an approx 675 sq foot retail/office room with a separate entrance at the driveway, a 28' x 53' post and beam barn with a full walkout lower level, a large pond, stone walls, incredible perennial garden surround, and a 21' x 45' accessory building with heat - great guest house or in-law potential. Inspired by Tuscan villas, Italianate style homes, usually square and symmetrical, were popular in the late 19th C. in New England. Park-like grounds; large pond has goldfish (see pics). The 3532 square foot main home has potential for an in-home business, or retail shop as it once was. Other potential uses in this highly-visible location include using the barn for farm animals and/or horses. Home has 4 bedrooms, 2 full bathrooms, 3 fireplaces, and approx 435 sq foot foot, renovated, eat-in, sunny kitchen with leathered granite counters and stainless appliances. New oil furnace 2026. Septic recently maintained (new pump, piping, and floats in 2022 by Garrity, no problems since). 50 gallon water heater Oct 2022. Substantial moldings and built-ins, front and back staircases, specialty stainless skylights, and a rooftop belvedere, which looks beautiful lit up at night, atop the well maintained copper roof. Minutes to three towns centers of Woodbury, Watertown, and Bethlehem. Guesthouse has elec.

1917 Main St N, Woodbury
$650,000
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

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