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

4 Beds ⋅ 3 Baths ⋅ 24160671 MLS

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

74 Middle Quarter Rd, Woodbury

$665,000

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

4 Beds ⋅ 3 Baths ⋅ 24130704 MLS

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

174 Weekeepeemee Rd, Woodbury

$660,000

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

3 Beds ⋅ 3 Baths ⋅ 24125016 MLS

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

38 Barnhill Rd, Woodbury

$655,000

Best buy in all of Woodbury (Syosset Schools). Live in the prestigious community of Woodbury Village. With full amenities, pool and tennis courts and playground, snow/garbage removal, and landscaping. Close to shopping, restaurants, schools, LIRR. Top location. 2 bedrooms, 1.5 bath, Eat-in-kitchen, patio deck, parking, CAC and central heating. Storage in pull down attic. Enjoy country club living.

2 Beds ⋅ 2 Baths ⋅ 946923 MLS

Best buy in all of Woodbury (Syosset Schools). Live in the prestigious community of Woodbury Village. With full amenities, pool and tennis courts and playground, snow/garbage removal, and landscaping. Close to shopping, restaurants, schools, LIRR. Top location. 2 bedrooms, 1.5 bath, Eat-in-kitchen, patio deck, parking, CAC and central heating. Storage in pull down attic. Enjoy country club living.

10 Hampton Way, Woodbury

$650,000

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

3 Beds ⋅ 2 Baths ⋅ 24173939 MLS

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

207 Grassy Hill Rd, Woodbury

$650,000

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

3 Beds ⋅ 3 Baths ⋅ 24147278 MLS

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

13 Park Ln, Woodbury

$640,000

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

3 Beds ⋅ 3 Baths ⋅ 24114993 MLS

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

32 Plumb Brook Rd, Woodbury

$635,000

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

4 Beds ⋅ 3 Baths ⋅ 24184647 MLS

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

20 Stagecoach Rd, Woodbury

$629,000

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

$625,000

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

3 Beds ⋅ 2 Baths ⋅ 24170889 MLS

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

54 School St, Woodbury

$615,000

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

3 Beds ⋅ 3 Baths ⋅ 24099745 MLS

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

130 Grassy Hill Rd, Woodbury

$612,500

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

$605,000

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

$605,000

Nestled on a peaceful cul-de-sac in Highland Mills, this spacious colonial offers both comfort and convenience. The main floor features two kitchens, perfect for multi-generational living or hosting guests, along with a first-floor bedroom and bath, creating a mini-suite for added privacy. Upstairs, you'll find a large primary bedroom with an en-suite bathroom, along with three additional well-sized bedrooms. The finished basement provides ample space for recreation, home office, or additional storage, making it an ideal flexible living area. Recent updates include fresh paint, new appliances, and several other improvements, ensuring the home is move-in ready. The property sits on a generous lot, perfect for entertaining, gardening, or simply relaxing in a serene outdoor space. Located close to a variety of outdoor recreational activities, sports, and major highways, this home offers the perfect blend of tranquility and accessibility. Don't miss the chance to make this Highland Mills gem your own!

5 Beds ⋅ 4 Baths ⋅ 981295 MLS

Nestled on a peaceful cul-de-sac in Highland Mills, this spacious colonial offers both comfort and convenience. The main floor features two kitchens, perfect for multi-generational living or hosting guests, along with a first-floor bedroom and bath, creating a mini-suite for added privacy. Upstairs, you'll find a large primary bedroom with an en-suite bathroom, along with three additional well-sized bedrooms. The finished basement provides ample space for recreation, home office, or additional storage, making it an ideal flexible living area. Recent updates include fresh paint, new appliances, and several other improvements, ensuring the home is move-in ready. The property sits on a generous lot, perfect for entertaining, gardening, or simply relaxing in a serene outdoor space. Located close to a variety of outdoor recreational activities, sports, and major highways, this home offers the perfect blend of tranquility and accessibility. Don't miss the chance to make this Highland Mills gem your own!

10 Leone Court, Woodbury

$600,000

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

$600,000

Welcome to your North Woodbury bucolic retreat! Escape from it all, nestled along the banks of the Weekeepeemee River with southern views and sunsets falling over the open fields, Heron fishing only yards from your Adirondack chair and Eagles perched on the nearby trees. Yes, this is Home. This 1780 Colonial has been well cared for, for many decades. The first floor offers a large updated kitchen with BRAND NEW appliances, formal dining room, living/entertaining room, study, parlor, and water closet. Four fireplaces are located on this level. Both a front and rear staircase will take you to the second level, five rooms in total, four currently being used as bedrooms and one as an office. There are two full bathrooms on the second level. A detached two-car garage with potting/storage room also has an additional finished and heated 720 square feet above. Situated 5 minutes to Woodbury Center, 10 mins to Washington Center, and 15 to Southbury/I-84.

4 Beds ⋅ 3 Baths ⋅ 24088739 MLS

Welcome to your North Woodbury bucolic retreat! Escape from it all, nestled along the banks of the Weekeepeemee River with southern views and sunsets falling over the open fields, Heron fishing only yards from your Adirondack chair and Eagles perched on the nearby trees. Yes, this is Home. This 1780 Colonial has been well cared for, for many decades. The first floor offers a large updated kitchen with BRAND NEW appliances, formal dining room, living/entertaining room, study, parlor, and water closet. Four fireplaces are located on this level. Both a front and rear staircase will take you to the second level, five rooms in total, four currently being used as bedrooms and one as an office. There are two full bathrooms on the second level. A detached two-car garage with potting/storage room also has an additional finished and heated 720 square feet above. Situated 5 minutes to Woodbury Center, 10 mins to Washington Center, and 15 to Southbury/I-84.

329 Weekeepeemee Rd, Woodbury

$600,000

Wonderful, spacious 3 bedroom 2.5 bath ranch on an open, level 1.3 acre lot. Sited on a quiet street that is still convenient to town, the home sits well back from the road and also offers a large private backyard. From the foyer one is greeted by an L shaped living and dining area with lots of large windows and an abundance of natural light. The eat-in kitchen features wood cabinets, plenty of counter space and stairs to the basement and backyard. The primary bedroom suite includes his/hers closets and a full bath. Across the hall are two more bedrooms and another full bath. Nearby is the den which has a fireplace and slider to the backyard. The 2 car garage is extra long offering storage for additional vehicles or equipment. The basement is unfinished but does have a convenient half bath. The stone patio off the rear of the home is gorgeous!

3 Beds ⋅ 3 Baths ⋅ 24126586 MLS

Wonderful, spacious 3 bedroom 2.5 bath ranch on an open, level 1.3 acre lot. Sited on a quiet street that is still convenient to town, the home sits well back from the road and also offers a large private backyard. From the foyer one is greeted by an L shaped living and dining area with lots of large windows and an abundance of natural light. The eat-in kitchen features wood cabinets, plenty of counter space and stairs to the basement and backyard. The primary bedroom suite includes his/hers closets and a full bath. Across the hall are two more bedrooms and another full bath. Nearby is the den which has a fireplace and slider to the backyard. The 2 car garage is extra long offering storage for additional vehicles or equipment. The basement is unfinished but does have a convenient half bath. The stone patio off the rear of the home is gorgeous!

36 Heritage Dr, Woodbury

$595,000

Welcome to this charming, single level ranch style home in idyllic Woodbury, one of Litchfield County's most desirable towns. With a wrap-around pea stone driveway and a long front porch, you get the best of Woodbury's rural qualities while also being close to convenient amenities. This property has an additional driveway that wraps around the side of the house to an oversized 2 car under-house garage, along with a storage shed and more closed-in storage under the large deck. The main level boasts just over 2,000sqft of true single level ranch living! Downstairs, you'll find an additional 700sqft of light, open, basement living space with a walkout sliding glass door to large private stone patio. This basement has the potential for an In-Law adaptation. There is a Washer and Dryer on both levels. With hardwood floors throughout, the main level is bright, clean, spacious, and functional. From the formal living room and dining room off of the entrance through the kitchen into the cozy family room with a gas fireplace, this custom ranch was designed with practicality and convenience alike! The large primary bedroom contains a standard sized closet, an additional walk-in closet, and an en-suite full bathroom. Come take a look and discover the charm of this home for yourself! This property is subject to Probate Approval and is sold in "As-Is" condition.

3 Beds ⋅ 2 Baths ⋅ 24129575 MLS

Welcome to this charming, single level ranch style home in idyllic Woodbury, one of Litchfield County's most desirable towns. With a wrap-around pea stone driveway and a long front porch, you get the best of Woodbury's rural qualities while also being close to convenient amenities. This property has an additional driveway that wraps around the side of the house to an oversized 2 car under-house garage, along with a storage shed and more closed-in storage under the large deck. The main level boasts just over 2,000sqft of true single level ranch living! Downstairs, you'll find an additional 700sqft of light, open, basement living space with a walkout sliding glass door to large private stone patio. This basement has the potential for an In-Law adaptation. There is a Washer and Dryer on both levels. With hardwood floors throughout, the main level is bright, clean, spacious, and functional. From the formal living room and dining room off of the entrance through the kitchen into the cozy family room with a gas fireplace, this custom ranch was designed with practicality and convenience alike! The large primary bedroom contains a standard sized closet, an additional walk-in closet, and an en-suite full bathroom. Come take a look and discover the charm of this home for yourself! This property is subject to Probate Approval and is sold in "As-Is" condition.

90 Railtree Hill Rd, Woodbury

$592,750

Built in 1900 as a barn and converted to a home in 1990, the architecture fuses countryside charm and mid-century design - two contrasting genres married to create an interesting and unique experience. The home is entered via an offset entry that opens into an all-seasons sunken sunroom overlooking the expansive backyard. You flow directly into the eat-in kitchen, which is outfitted with maple cabinetry. As you ease down the hall, you'll pass a bedroom, a full bath, and an office. The final room is the living room, highlighting the mid-century style element of bringing the outdoors in with floor-to-ceiling windows across the entire back wall. The home's placement at the uppermost portion of the acreage allows for views that fill the windows, creating a sense of space and openness. The living room has two stair passages, one leading to the ground-level apartment and the other to the sleeping quarters on the second floor. The staircase which leads to the second floor has a small loft which overlooks the living room and leads to three bedrooms and a shared bath . The primary suite mirrors the living room with wall-to-wall windows overlooking the verdant acreage. The lower, ground level has a complete apartment with a private exterior entry for guests or rental potential. The foundation for a breathtaking Litchfield County home is here, welcoming your imagination and eye for design.

6 Beds ⋅ 3 Baths ⋅ 24118623 MLS

Built in 1900 as a barn and converted to a home in 1990, the architecture fuses countryside charm and mid-century design - two contrasting genres married to create an interesting and unique experience. The home is entered via an offset entry that opens into an all-seasons sunken sunroom overlooking the expansive backyard. You flow directly into the eat-in kitchen, which is outfitted with maple cabinetry. As you ease down the hall, you'll pass a bedroom, a full bath, and an office. The final room is the living room, highlighting the mid-century style element of bringing the outdoors in with floor-to-ceiling windows across the entire back wall. The home's placement at the uppermost portion of the acreage allows for views that fill the windows, creating a sense of space and openness. The living room has two stair passages, one leading to the ground-level apartment and the other to the sleeping quarters on the second floor. The staircase which leads to the second floor has a small loft which overlooks the living room and leads to three bedrooms and a shared bath . The primary suite mirrors the living room with wall-to-wall windows overlooking the verdant acreage. The lower, ground level has a complete apartment with a private exterior entry for guests or rental potential. The foundation for a breathtaking Litchfield County home is here, welcoming your imagination and eye for design.

94 Old Town Farm Rd, Woodbury

$590,000

Offered for the first time, this custom-built Cape was carefully designed with a vision for both comfortable living and future expansion. Currently configured for easy one-level living, the home features a spacious, well-built layout with hardwood floors and generously proportioned rooms throughout. Upstairs, a blank canvas awaits-ready to become additional bedrooms, a full bath, and expanded living space above the two-car garage. Whether you follow the original plans or create your own vision, the possibilities here are truly exceptional. Set on over 3 acres in one of Woodbury's most sought-after locations, the property is rich with character-featuring classic fieldstone walls, mature gardens, and enduring curb appeal with a composite slate roof and low-maintenance exterior. Unwind on the three-season porch, or gather by the fireplace and enjoy the warmth of a home designed to grow with you. This is a rare chance to create something special in a beautiful setting.

1 Beds ⋅ 2 Baths ⋅ 24153133 MLS

Offered for the first time, this custom-built Cape was carefully designed with a vision for both comfortable living and future expansion. Currently configured for easy one-level living, the home features a spacious, well-built layout with hardwood floors and generously proportioned rooms throughout. Upstairs, a blank canvas awaits-ready to become additional bedrooms, a full bath, and expanded living space above the two-car garage. Whether you follow the original plans or create your own vision, the possibilities here are truly exceptional. Set on over 3 acres in one of Woodbury's most sought-after locations, the property is rich with character-featuring classic fieldstone walls, mature gardens, and enduring curb appeal with a composite slate roof and low-maintenance exterior. Unwind on the three-season porch, or gather by the fireplace and enjoy the warmth of a home designed to grow with you. This is a rare chance to create something special in a beautiful setting.

123 Cross Brook Rd, Woodbury

$585,000

Beautifully renovated and move-in ready, this stand-alone unit in the charming Woodbury Hill condominium community offers a bright, open floor plan and the convenience of first-floor living. Hardwood floors run throughout, while the expanded living room features a cathedral ceiling and dramatic floor-to-ceiling brick fireplace. The completely renovated kitchen opens to the dining room, creating an easy flow for everyday living and entertaining. Sliders lead to a private deck and small patio overlooking the backyard. The first-floor primary suite includes a walk-in closet and full bath. Upstairs, the sought-after loft provides flexible space for an office, den, or TV room, along with a second spacious bedroom and full bath. A finished lower-level room offers additional living space, while the attached two-car garage and full basement provide excellent storage. A beautifully updated home in one of Woodbury's most desirable condominium communities.

2 Beds ⋅ 3 Baths ⋅ 24201487 MLS ⋅ Woodbury Hill BLDG.

Beautifully renovated and move-in ready, this stand-alone unit in the charming Woodbury Hill condominium community offers a bright, open floor plan and the convenience of first-floor living. Hardwood floors run throughout, while the expanded living room features a cathedral ceiling and dramatic floor-to-ceiling brick fireplace. The completely renovated kitchen opens to the dining room, creating an easy flow for everyday living and entertaining. Sliders lead to a private deck and small patio overlooking the backyard. The first-floor primary suite includes a walk-in closet and full bath. Upstairs, the sought-after loft provides flexible space for an office, den, or TV room, along with a second spacious bedroom and full bath. A finished lower-level room offers additional living space, while the attached two-car garage and full basement provide excellent storage. A beautifully updated home in one of Woodbury's most desirable condominium communities.

25 Woodbury Hill, Unit 25, Woodbury

$580,000

Nestled on 1.53 acres and set back from the road, this charming Cape Cod style home offers the perfect blend of comfort, character and New England charm. The interior features 2 bedrooms and a full bath on the main and upper level. An inviting Living Room showcases a fireplace with an energy efficient woodburning insert, creating a warm and cozy gathering space. The dining area provides access to the 14x8 rear deck, ideal for outdoor entertaining or relaxing while enjoying the peaceful surroundings. The kitchen includes an island, LVP flooring and ample workspace. Hardwood floors throughout most of the home. Additional highlights include a newer propane heating system with on demand hot water, full basement with interior and garage access, Generator-ready wired for peace of mind and 2 car under house garage with auto door openers. Outside you'll find a 10x10 storage shed and recently paved driveway. Just minutes from Woodbury's vibrant Main Street is easy access to enjoy shopping, dining, the library, post office, parks and scenic land preserves for outdoor activities. Whether you're seeking full-time residence or a weekend getaway, this property offers a great opportunity in one of Connecticut's picturesque communities and "Antique Capitol". Ideally situated roughly 80 miles from NYC approximately 140 miles from Boston.

4 Beds ⋅ 2 Baths ⋅ 24179676 MLS

Nestled on 1.53 acres and set back from the road, this charming Cape Cod style home offers the perfect blend of comfort, character and New England charm. The interior features 2 bedrooms and a full bath on the main and upper level. An inviting Living Room showcases a fireplace with an energy efficient woodburning insert, creating a warm and cozy gathering space. The dining area provides access to the 14x8 rear deck, ideal for outdoor entertaining or relaxing while enjoying the peaceful surroundings. The kitchen includes an island, LVP flooring and ample workspace. Hardwood floors throughout most of the home. Additional highlights include a newer propane heating system with on demand hot water, full basement with interior and garage access, Generator-ready wired for peace of mind and 2 car under house garage with auto door openers. Outside you'll find a 10x10 storage shed and recently paved driveway. Just minutes from Woodbury's vibrant Main Street is easy access to enjoy shopping, dining, the library, post office, parks and scenic land preserves for outdoor activities. Whether you're seeking full-time residence or a weekend getaway, this property offers a great opportunity in one of Connecticut's picturesque communities and "Antique Capitol". Ideally situated roughly 80 miles from NYC approximately 140 miles from Boston.

338 Good Hill Rd, Woodbury

$580,000

The epitome of where Contemporary Design, open spaces, light and efficiency meet the true warmth and pride of local master craftsman. If 9 secluded acres is not peace and privacy enough, your abutting neighbor is 128 acres of protected land owned by Flanders Nature Center. Live amongst the trees and fabulous backdrop of rock outcroppings. Some selective clearing could bring back distant mountain top views. Keep it local, keep it grounded...Bob Keating design, a local architect with a love of nature and minimal wall spaces. Guy Wolf designed, milled and laid all of the wide board oak, cherry and maple flooring. Woody Mosche crafted the bespoke Ash kitchen cabinetry and the cherry wet bar in the sunken great room. The great room focal points are the 26' exposed brick chimney against the soaring beamed ceiling as well as the sliders and numerous windows that bring nature inside. Two bedrooms on the main level and a wonderful primary suite encompasses the entire second level, complete w reading/office loft. The hiking trails that pass the three seasonal ponds have since faded and nature is just waiting for new curators to explore. Nine private acres gives you the potential to expand the existing home, or build another on the property for a family compound. The home calls to people who want a total seclusion from the world yet only a five minute drive into historic Woodbury with all its history, arts, charm and fabulous restaurants.

3 Beds ⋅ 2 Baths ⋅ 24120744 MLS

The epitome of where Contemporary Design, open spaces, light and efficiency meet the true warmth and pride of local master craftsman. If 9 secluded acres is not peace and privacy enough, your abutting neighbor is 128 acres of protected land owned by Flanders Nature Center. Live amongst the trees and fabulous backdrop of rock outcroppings. Some selective clearing could bring back distant mountain top views. Keep it local, keep it grounded...Bob Keating design, a local architect with a love of nature and minimal wall spaces. Guy Wolf designed, milled and laid all of the wide board oak, cherry and maple flooring. Woody Mosche crafted the bespoke Ash kitchen cabinetry and the cherry wet bar in the sunken great room. The great room focal points are the 26' exposed brick chimney against the soaring beamed ceiling as well as the sliders and numerous windows that bring nature inside. Two bedrooms on the main level and a wonderful primary suite encompasses the entire second level, complete w reading/office loft. The hiking trails that pass the three seasonal ponds have since faded and nature is just waiting for new curators to explore. Nine private acres gives you the potential to expand the existing home, or build another on the property for a family compound. The home calls to people who want a total seclusion from the world yet only a five minute drive into historic Woodbury with all its history, arts, charm and fabulous restaurants.

101 Plumb Brook Rd, 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

$575,000

Charm and modern comfort come together in this beautifully renovated 3-bedroom, 2-bath home set on nearly an acre along a quiet country road in Woodbury. Thoughtfully updated and move-in ready, this inviting home blends classic New England character with practical improvements throughout, including a fully insulated attic and insulated walls added by the current owner for enhanced comfort and efficiency. The main level features a warm living room with fireplace, a spacious first-floor bedroom, and a full bath, offering flexibility for guests or convenient one-level living. The newly updated kitchen opens to the dining area and leads directly to a brand-new deck overlooking a private, level backyard with distant pond and mountain views. The yard has been cleared and extends to a peaceful meadow that backs to a wooded preserve, creating a serene and private setting. A recent expansion added an oversized two-car garage, extra deep with high ceilings and potential for a loft, workshop, or additional storage. The full basement offers tall ceilings, ample storage, and rear exterior access to the leveled backyard. Adjacent to the basement door is an additional versatile room, ideal for outdoor storage, tools, hobbies, or a creative workspace.

3 Beds ⋅ 2 Baths ⋅ 24172678 MLS

Charm and modern comfort come together in this beautifully renovated 3-bedroom, 2-bath home set on nearly an acre along a quiet country road in Woodbury. Thoughtfully updated and move-in ready, this inviting home blends classic New England character with practical improvements throughout, including a fully insulated attic and insulated walls added by the current owner for enhanced comfort and efficiency. The main level features a warm living room with fireplace, a spacious first-floor bedroom, and a full bath, offering flexibility for guests or convenient one-level living. The newly updated kitchen opens to the dining area and leads directly to a brand-new deck overlooking a private, level backyard with distant pond and mountain views. The yard has been cleared and extends to a peaceful meadow that backs to a wooded preserve, creating a serene and private setting. A recent expansion added an oversized two-car garage, extra deep with high ceilings and potential for a loft, workshop, or additional storage. The full basement offers tall ceilings, ample storage, and rear exterior access to the leveled backyard. Adjacent to the basement door is an additional versatile room, ideal for outdoor storage, tools, hobbies, or a creative workspace.

2 Judd Hill Rd, Woodbury

$570,000

Classic early-1900s colonial in the heart of Woodbury with 3 bedrooms, 2 full baths, and over 1,900 square feet of living space. The home offers a comfortable mix of older-home character and practical updates, with hardwood floors, good natural light, and a layout that works well for everyday living. The updated kitchen features white cabinetry, granite counters, stainless steel appliances, recessed lighting, and a breakfast bar area. It has a clean, bright feel with plenty of cabinet and counter space. The living room offers a warm, traditional setting with hardwood floors, a brick fireplace, and large windows overlooking the property. Outside, the home sits back from the road with a large paved driveway and a detached 2-car garage. The garage provides great storage, parking, and separate workspace potential. Additional features include a full basement, newer well, and a whole-house generator. This is a solid Woodbury home with historic charm, useful updates, and a convenient location close to town, shops, restaurants, and area amenities.

3 Beds ⋅ 2 Baths ⋅ 24175070 MLS

Classic early-1900s colonial in the heart of Woodbury with 3 bedrooms, 2 full baths, and over 1,900 square feet of living space. The home offers a comfortable mix of older-home character and practical updates, with hardwood floors, good natural light, and a layout that works well for everyday living. The updated kitchen features white cabinetry, granite counters, stainless steel appliances, recessed lighting, and a breakfast bar area. It has a clean, bright feel with plenty of cabinet and counter space. The living room offers a warm, traditional setting with hardwood floors, a brick fireplace, and large windows overlooking the property. Outside, the home sits back from the road with a large paved driveway and a detached 2-car garage. The garage provides great storage, parking, and separate workspace potential. Additional features include a full basement, newer well, and a whole-house generator. This is a solid Woodbury home with historic charm, useful updates, and a convenient location close to town, shops, restaurants, and area amenities.

5 Westwood Rd, Woodbury

$559,000

You won't believe your eyes! Come and see this stunning, newly renovated cozy house located in a quiet neighborhood, yet close to all community amenities and shopping areas. This property sits on nearly half an acre of land and features brand new stone countertops in the kitchen, which is designed with elegant spotlights throughout the house. The home boasts five oversized bedrooms, each with a spacious walk-in/closet, and there are 2 and a half bathrooms. Additionally, you'll find a lovely family bonus room in the finished basement, complete with full above-ground windows that let in plenty of natural light. Enjoy the beauty of nature that surrounds this house as you step out onto a large, beautiful deck. The newly paved driveway adds to its charm. You are more than welcome to come and see it for yourself. Don't miss out on this amazing opportunity—schedule your visit today before it's gone!

5 Beds ⋅ 3 Baths ⋅ 921211 MLS

You won't believe your eyes! Come and see this stunning, newly renovated cozy house located in a quiet neighborhood, yet close to all community amenities and shopping areas. This property sits on nearly half an acre of land and features brand new stone countertops in the kitchen, which is designed with elegant spotlights throughout the house. The home boasts five oversized bedrooms, each with a spacious walk-in/closet, and there are 2 and a half bathrooms. Additionally, you'll find a lovely family bonus room in the finished basement, complete with full above-ground windows that let in plenty of natural light. Enjoy the beauty of nature that surrounds this house as you step out onto a large, beautiful deck. The newly paved driveway adds to its charm. You are more than welcome to come and see it for yourself. Don't miss out on this amazing opportunity—schedule your visit today before it's gone!

3 Carroll Drive, Woodbury

$550,000

Charm and modern comfort come together in this beautifully renovated 3BR, 2BA home set on nearly an acre along a quiet country road in Woodbury. The inviting main level features a cozy living room with a fireplace, a spacious first-floor bedroom, and a full bath-perfect for guests or one-level living. A newly updated kitchen opens to the dining area and leads directly to a brand-new deck overlooking a private, level backyard with distant pond and mountain views. The yard has been cleared, seeded, and extends to a peaceful meadow that backs to a wooded preserve. The recent expansion includes an oversized two-car garage, extra deep with high ceilings offering loft or workshop potential. The full basement offers tall ceilings, ample storage, and rear exterior access to the leveled backyard. Adjacent to the basement door is an additional versatile room ideal for outdoor storage, tools, or a creative workspace. Move-in ready and turn-key, this home blends New England charm with thoughtful updates and serene surroundings that will certainly delight everyone who walks through the door of this one of a kind home situated on an extremely private lot. Come see it and don't miss this opportunity to own an oasis in Woodbury. Added highlights include a new furnace (2025), new septic tank (2025), newer whole-house propane generator, and a roof approximately 10 years old.

3 Beds ⋅ 2 Baths ⋅ 24134430 MLS

Charm and modern comfort come together in this beautifully renovated 3BR, 2BA home set on nearly an acre along a quiet country road in Woodbury. The inviting main level features a cozy living room with a fireplace, a spacious first-floor bedroom, and a full bath-perfect for guests or one-level living. A newly updated kitchen opens to the dining area and leads directly to a brand-new deck overlooking a private, level backyard with distant pond and mountain views. The yard has been cleared, seeded, and extends to a peaceful meadow that backs to a wooded preserve. The recent expansion includes an oversized two-car garage, extra deep with high ceilings offering loft or workshop potential. The full basement offers tall ceilings, ample storage, and rear exterior access to the leveled backyard. Adjacent to the basement door is an additional versatile room ideal for outdoor storage, tools, or a creative workspace. Move-in ready and turn-key, this home blends New England charm with thoughtful updates and serene surroundings that will certainly delight everyone who walks through the door of this one of a kind home situated on an extremely private lot. Come see it and don't miss this opportunity to own an oasis in Woodbury. Added highlights include a new furnace (2025), new septic tank (2025), newer whole-house propane generator, and a roof approximately 10 years old.

2 Judd Hill Rd, Woodbury

$550,000

Charming antique home in the heart of Woodbury! Set on a spacious, cleared lot, this beautifully maintained property offers a perfect mix of historic character and modern updates. The kitchen features quartz countertops, stainless steel appliances, and ample cabinetry. With three full baths and a large primary suite with walk-in closet and private bath, comfort and convenience abound. Enjoy the serene sunroom overlooking the expansive yard-ideal for relaxation or entertaining. A classic barn with a loft and finished office space adds versatility for hobbies, storage, or remote work. Just a short walk to the town center, this unique home is a rare opportunity to own a piece of New England charm with today's amenities.

4 Beds ⋅ 3 Baths ⋅ 24091687 MLS

Charming antique home in the heart of Woodbury! Set on a spacious, cleared lot, this beautifully maintained property offers a perfect mix of historic character and modern updates. The kitchen features quartz countertops, stainless steel appliances, and ample cabinetry. With three full baths and a large primary suite with walk-in closet and private bath, comfort and convenience abound. Enjoy the serene sunroom overlooking the expansive yard-ideal for relaxation or entertaining. A classic barn with a loft and finished office space adds versatility for hobbies, storage, or remote work. Just a short walk to the town center, this unique home is a rare opportunity to own a piece of New England charm with today's amenities.

212 Main St N, Woodbury

$547,500

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

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