Currantlyhome.com Search Results

$1,395,000

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.

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

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!

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

Welcome to 17 Curtiss Drive! 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

3 Beds ⋅ 3 Baths ⋅ 24192675 MLS

Welcome to 17 Curtiss Drive! 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

$398,000

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.

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

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!

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

$1,100,000

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.

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

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.

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

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.

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

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.

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

$895,000

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.

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

$495,000

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.

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

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!

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

$799,900

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.

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

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!

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

$1,790,000

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.

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

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.

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

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.

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

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.

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

$2,995,000

Warren's Landing on the Pomperaug is an extraordinary estate where historic character is centered around a beautifully preserved 1890 Greek Revival residence. The home offers four bedrooms, timeless architectural details, spacious rooms, 4 fireplaces and custom built-ins. The impressive six-barn complex provides exceptional flexibility, featuring a retail shop, extensive equipment storage, a two-car garage, pool cabana and pool equipment building. A newly constructed temperature controlled 3,800-square-foot post-and-beam barn with a half bath and laundry room at the rear of the property further expand the property's possibilities. There are also an equipment/horse barn and riverside cabin. Outdoor living is equally remarkable with a stunning new in-ground gunite pool surrounded by lush landscaping. Designed for both relaxation and entertaining, the grounds include a custom "summer kitchen" with a European-style outdoor pizza oven, gas grill, and screened dining pavilion-perfect for hosting gatherings or enjoying quiet evenings. The 18.3-acre setting includes mature trees, open meadows, scenic walking trails, and frontage along the protected Pomperaug River, creating a private and picturesque retreat. Rich in history yet thoughtfully updated, this rare estate offers an exceptional combination of beauty, functionality, and enduring charm. A comprehensive list of recent improvements is available upon request. Buyer must do due diligence with the town for possible uses.

4 Beds ⋅ 6 Baths ⋅ 24163576 MLS

Warren's Landing on the Pomperaug is an extraordinary estate where historic character is centered around a beautifully preserved 1890 Greek Revival residence. The home offers four bedrooms, timeless architectural details, spacious rooms, 4 fireplaces and custom built-ins. The impressive six-barn complex provides exceptional flexibility, featuring a retail shop, extensive equipment storage, a two-car garage, pool cabana and pool equipment building. A newly constructed temperature controlled 3,800-square-foot post-and-beam barn with a half bath and laundry room at the rear of the property further expand the property's possibilities. There are also an equipment/horse barn and riverside cabin. Outdoor living is equally remarkable with a stunning new in-ground gunite pool surrounded by lush landscaping. Designed for both relaxation and entertaining, the grounds include a custom "summer kitchen" with a European-style outdoor pizza oven, gas grill, and screened dining pavilion-perfect for hosting gatherings or enjoying quiet evenings. The 18.3-acre setting includes mature trees, open meadows, scenic walking trails, and frontage along the protected Pomperaug River, creating a private and picturesque retreat. Rich in history yet thoughtfully updated, this rare estate offers an exceptional combination of beauty, functionality, and enduring charm. A comprehensive list of recent improvements is available upon request. Buyer must do due diligence with the town for possible uses.

920 Main St S, Woodbury

$525,000

Nestled in the well-established Sherman Hill neighborhood, this five-bedroom home offers a generous footprint to put your personal touches on. Boasting wood flooring and newer windows throughout, the main level features a fluid layout designed for effortless living: a spacious living room, formal dining room, an eat-in kitchen, a cozy family room with a fireplace, a private home office, and a convenient full bath. Upstairs, you'll find five sizable bedrooms, including a primary suite complete with two walk-in closets and a private full bath. The remaining four bedrooms share a large full bathroom equipped with a double vanity. The expansive walk-out lower level adds incredible value with over 1,000 square feet of finished, heated living space. Create a game room with the provided pool table and a den area with a second fireplace, or utilize it as a potential in-law suite as light streams through a large picture window with views of the backyard. Outside, a stately circular driveway frames the property amidst mature, private landscaping, while the back deck is primed for summer grilling. Complete with an oversized two-car garage featuring a dedicated work area and abundant storage closets, this home is ready for you to bring your design ideas and unlock its full potential!

5 Beds ⋅ 3 Baths ⋅ 24181554 MLS

Nestled in the well-established Sherman Hill neighborhood, this five-bedroom home offers a generous footprint to put your personal touches on. Boasting wood flooring and newer windows throughout, the main level features a fluid layout designed for effortless living: a spacious living room, formal dining room, an eat-in kitchen, a cozy family room with a fireplace, a private home office, and a convenient full bath. Upstairs, you'll find five sizable bedrooms, including a primary suite complete with two walk-in closets and a private full bath. The remaining four bedrooms share a large full bathroom equipped with a double vanity. The expansive walk-out lower level adds incredible value with over 1,000 square feet of finished, heated living space. Create a game room with the provided pool table and a den area with a second fireplace, or utilize it as a potential in-law suite as light streams through a large picture window with views of the backyard. Outside, a stately circular driveway frames the property amidst mature, private landscaping, while the back deck is primed for summer grilling. Complete with an oversized two-car garage featuring a dedicated work area and abundant storage closets, this home is ready for you to bring your design ideas and unlock its full potential!

33 Hurds Hill Rd, Woodbury

$259,000

** INVESTORS TAKE NOTICE! ** Nestled in the desirable town of Woodbury, this 3 bedroom, 1.5 bath Colonial presents a unique opportunity to restore and reimagine a property full of charm and potential. Featuring hardwood flooring throughout the majority, spacious interiors, newer appliances, and some more recently installed mechanicals, this home offers a solid foundation for renovation and personalization. A remarkable oversized barn/garage adds tremendous value and versatility. This space is ideal for contractors, collectors, a workshop space, storage, hobbyists, and many other possibilities. The peaceful setting, mature landscape, and generous lot size create the perfect backdrop for a thoughtful transformation. Whether you're an investor, flipper, or buyer with a vision, this property offers the chance to unlock significant potential in a highly sought-after Woodbury location. Property is being conveyed as-is.

3 Beds ⋅ 2 Baths ⋅ 24179875 MLS

** INVESTORS TAKE NOTICE! ** Nestled in the desirable town of Woodbury, this 3 bedroom, 1.5 bath Colonial presents a unique opportunity to restore and reimagine a property full of charm and potential. Featuring hardwood flooring throughout the majority, spacious interiors, newer appliances, and some more recently installed mechanicals, this home offers a solid foundation for renovation and personalization. A remarkable oversized barn/garage adds tremendous value and versatility. This space is ideal for contractors, collectors, a workshop space, storage, hobbyists, and many other possibilities. The peaceful setting, mature landscape, and generous lot size create the perfect backdrop for a thoughtful transformation. Whether you're an investor, flipper, or buyer with a vision, this property offers the chance to unlock significant potential in a highly sought-after Woodbury location. Property is being conveyed as-is.

6 Easy St, Woodbury

$425,000

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.

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

$649,900

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!

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

$775,000

The Orton-Martin Homestead. One of Woodbury's oldest homes has been updated for today's lifestyle. History surrounds you with wide board flooring, library built-ins, two fireplaces and 1850 barn. This four -bedroom home offers spacious rooms, three finished levels and hidden delights. Enjoy picnics under the mature trees on your own fenced-in level yard. Sidewalks take you everywhere on Main St where you can enjoy the Library, antique and retail shops, schools, churches, great restaurants and coffee shops. Parks and the Senior Center are all nearby. Only 90 minutes to NYC. Named by Reader's Digest as one of CT most charming towns. Come call Woodbury home!

4 Beds ⋅ 4 Baths ⋅ 24138386 MLS

The Orton-Martin Homestead. One of Woodbury's oldest homes has been updated for today's lifestyle. History surrounds you with wide board flooring, library built-ins, two fireplaces and 1850 barn. This four -bedroom home offers spacious rooms, three finished levels and hidden delights. Enjoy picnics under the mature trees on your own fenced-in level yard. Sidewalks take you everywhere on Main St where you can enjoy the Library, antique and retail shops, schools, churches, great restaurants and coffee shops. Parks and the Senior Center are all nearby. Only 90 minutes to NYC. Named by Reader's Digest as one of CT most charming towns. Come call Woodbury home!

28 School St, Woodbury

$545,000

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.

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

$895,000

Welcome to Bacon Pond House. A seamless blend of 19th-century soul and 21st-century luxury. Situated on over 3 acres, this antique Colonial has been thoughtfully revived to honor its heritage while offering every modern convenience. The interior, lovingly brought back to life, features wide-plank flooring and exposed hand-hewn beams that anchor the home's historic character. The rooms are designed for both intimacy and entertaining. A cozy sitting room and a dedicated office/library-complete with a classic fireplace-offer quiet retreats. For larger gatherings, the front-to-back living room, with windows on three sides, is bathed in natural light. At the heart of the home is the remodeled kitchen, which opens to the dining room centered around the original refurbished center core fireplace. Upstairs, four bedrooms await. The primary bedroom offers a new ensuite bath detailed with custom tile. The three additional bedrooms share a fully renovated bathroom with a soaking tub/shower combo. Thoughtfully curated, professionally designed interior furniture and fixtures are available upon request. The property has benefited from extensive renovations that include new bathrooms and kitchen, floor refinishing, a new well, upgraded septic, and more; a substantial list is available upon request.

4 Beds ⋅ 3 Baths ⋅ 24172742 MLS

Welcome to Bacon Pond House. A seamless blend of 19th-century soul and 21st-century luxury. Situated on over 3 acres, this antique Colonial has been thoughtfully revived to honor its heritage while offering every modern convenience. The interior, lovingly brought back to life, features wide-plank flooring and exposed hand-hewn beams that anchor the home's historic character. The rooms are designed for both intimacy and entertaining. A cozy sitting room and a dedicated office/library-complete with a classic fireplace-offer quiet retreats. For larger gatherings, the front-to-back living room, with windows on three sides, is bathed in natural light. At the heart of the home is the remodeled kitchen, which opens to the dining room centered around the original refurbished center core fireplace. Upstairs, four bedrooms await. The primary bedroom offers a new ensuite bath detailed with custom tile. The three additional bedrooms share a fully renovated bathroom with a soaking tub/shower combo. Thoughtfully curated, professionally designed interior furniture and fixtures are available upon request. The property has benefited from extensive renovations that include new bathrooms and kitchen, floor refinishing, a new well, upgraded septic, and more; a substantial list is available upon request.

253 Bacon Pond Rd, Woodbury

$874,900

Beautiful Colonial set on a private 3+ acre lot in sought-after Curtiss Meadows, ideally located on the southern end of Woodbury abutting the Southbury line. Set back from the cul-de-sac entryway, this well-cared-for home offers a wonderful blend of privacy, comfort, convenience, and thoughtful updates. The level, light-filled driveway provides easy access, while the peaceful setting creates a true sense of retreat just minutes from Woodbury and Southbury town centers, commuting routes, and everyday amenities. Offering 3,865 sq. ft. of finished living space on the main two levels, plus an additional 550 sq. ft. recreation room in the walkout lower level, this spacious home provides plenty of room to live, work, and entertain. The first floor features a gourmet kitchen with granite countertops and a large center island perfect for gathering, a spacious great room with cathedral ceiling, formal living and dining rooms, and a cozy den with fireplace. Upstairs, an open foyer/sitting area leads to a comfortable primary suite and three generously sized bedrooms. The exterior is beautifully maintained and includes a privacy fence, rear patio, and three-car garage. Recent improvements add even more value, including a new HVAC and central air conditioning system installed in March 2026, along with solar panels added by the owners to help curb rising energy costs. The two fireplaces give wonderful comfort and warmth.

4 Beds ⋅ 5 Baths ⋅ 24172449 MLS

Beautiful Colonial set on a private 3+ acre lot in sought-after Curtiss Meadows, ideally located on the southern end of Woodbury abutting the Southbury line. Set back from the cul-de-sac entryway, this well-cared-for home offers a wonderful blend of privacy, comfort, convenience, and thoughtful updates. The level, light-filled driveway provides easy access, while the peaceful setting creates a true sense of retreat just minutes from Woodbury and Southbury town centers, commuting routes, and everyday amenities. Offering 3,865 sq. ft. of finished living space on the main two levels, plus an additional 550 sq. ft. recreation room in the walkout lower level, this spacious home provides plenty of room to live, work, and entertain. The first floor features a gourmet kitchen with granite countertops and a large center island perfect for gathering, a spacious great room with cathedral ceiling, formal living and dining rooms, and a cozy den with fireplace. Upstairs, an open foyer/sitting area leads to a comfortable primary suite and three generously sized bedrooms. The exterior is beautifully maintained and includes a privacy fence, rear patio, and three-car garage. Recent improvements add even more value, including a new HVAC and central air conditioning system installed in March 2026, along with solar panels added by the owners to help curb rising energy costs. The two fireplaces give wonderful comfort and warmth.

8 Curtiss Mdws, Woodbury

$645,000

QUAIL RUN On the cul de sac - 4 NEW HOMES 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! Construction has begun on 2 homes with anticipated completion in August. #94 is a 3 BR, 2.5 BA FARMHOUSE STYLE SPLIT LEVEL with large front porch, oversized 2 car garage, CATHEDRAL LIVING ROOM and finished lower level with laundry room and half bath.

3 Beds ⋅ 3 Baths ⋅ 24165212 MLS

QUAIL RUN On the cul de sac - 4 NEW HOMES 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! Construction has begun on 2 homes with anticipated completion in August. #94 is a 3 BR, 2.5 BA FARMHOUSE STYLE SPLIT LEVEL with large front porch, oversized 2 car garage, CATHEDRAL LIVING ROOM and finished lower level with laundry room and half bath.

94 Quail Run Rd, Woodbury

$765,000

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! Construction has begun with completion possible in early October. #86 is a 3 BR, 2.5 BA Cape with FULL FRONT PORCH, 2 car attached garage and OPEN BUT LIVABLE floor plan. LL set up for future finishing.

3 Beds ⋅ 3 Baths ⋅ 24159088 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! Construction has begun with completion possible in early October. #86 is a 3 BR, 2.5 BA Cape with FULL FRONT PORCH, 2 car attached garage and OPEN BUT LIVABLE floor plan. LL set up for future finishing.

86 Quail Run Rd, Woodbury

$1,495,000

Step through the doors of history and into one of Connecticut's most treasured colonial residences. Built in 1760 and proudly listed on the National Register of Historic Places, the Jabez Bacon House is a rare masterpiece of 18th-century American architecture that has endured with remarkable grace for over 260 years. This distinguished home has also been recognized for its exceptional preservation and character, having been featured in Early American Life magazine and Historic Homes magazine-an honor that speaks to its authenticity and enduring appeal. This stately five bedroom home showcases original architectural details that collectors and history enthusiasts dream about. Seven fireplaces anchor the home's character across its generous 4,800+ square feet. Five beautifully paneled rooms reveal the craftsmanship of a bygone era, while antique wide-board flooring runs throughout, whispering stories of centuries past beneath every footstep.

5 Beds ⋅ 5 Baths ⋅ 24168618 MLS

Step through the doors of history and into one of Connecticut's most treasured colonial residences. Built in 1760 and proudly listed on the National Register of Historic Places, the Jabez Bacon House is a rare masterpiece of 18th-century American architecture that has endured with remarkable grace for over 260 years. This distinguished home has also been recognized for its exceptional preservation and character, having been featured in Early American Life magazine and Historic Homes magazine-an honor that speaks to its authenticity and enduring appeal. This stately five bedroom home showcases original architectural details that collectors and history enthusiasts dream about. Seven fireplaces anchor the home's character across its generous 4,800+ square feet. Five beautifully paneled rooms reveal the craftsmanship of a bygone era, while antique wide-board flooring runs throughout, whispering stories of centuries past beneath every footstep.

30 Hollow, Woodbury