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Looking for the ease of one level living, a beautiful backyard, and the peace of mind that comes with major updates already completed? This Woodbury ranch checks all the boxes! Nestled along a quiet, country road, this meticulously maintained 3 bedroom ranch offers the perfect blend of comfort, convenience, and a picturesque setting. Pride of ownership shines throughout, featuring hardwood flooring, a bright and inviting interior, a spacious kitchen with white cabinetry and stainless steel appliances along with access to a newer deck, perfect for outdoor dining, entertaining, or enjoying your morning coffee. The expansive, backyard features mature trees, perennial gardens, & professionally landscaped grounds. A 1 car garage with attic storage and 3 additional sheds on the property offer plenty of space for tools, equipment, and seasonal items. Enjoy peace of mind with significant improvements including a BRAND NEW septic system, newer heating and cooling systems, roof, and water filtration system. Lovingly cared for and thoughtfully updated, this Woodbury home is ready for it's next chapter!

3 Beds ⋅ 1 Baths ⋅ 24215409 MLS

Looking for the ease of one level living, a beautiful backyard, and the peace of mind that comes with major updates already completed? This Woodbury ranch checks all the boxes! Nestled along a quiet, country road, this meticulously maintained 3 bedroom ranch offers the perfect blend of comfort, convenience, and a picturesque setting. Pride of ownership shines throughout, featuring hardwood flooring, a bright and inviting interior, a spacious kitchen with white cabinetry and stainless steel appliances along with access to a newer deck, perfect for outdoor dining, entertaining, or enjoying your morning coffee. The expansive, backyard features mature trees, perennial gardens, & professionally landscaped grounds. A 1 car garage with attic storage and 3 additional sheds on the property offer plenty of space for tools, equipment, and seasonal items. Enjoy peace of mind with significant improvements including a BRAND NEW septic system, newer heating and cooling systems, roof, and water filtration system. Lovingly cared for and thoughtfully updated, this Woodbury home is ready for it's next chapter!

36 Atwood Rd, Woodbury

$949,999

Welcome home to this spacious 3-bedroom, 2.5-bath townhouse-style home located in the highly sought-after Syosset School District! Ideally situated as a desirable corner unit on a quiet cul-de-sac, this home offers a bright and spacious layout with beautiful wood floors throughout the main living areas and carpeting only in the bedrooms. Features include Andersen windows throughout, central air, gas heat, a cozy fireplace, attached garage, and pull-down attic offering additional storage. Step outside to a beautiful brand-new private patio, perfect for relaxing or entertaining. Enjoy fantastic community amenities including a swimming pool, tennis courts, playground, and more. Pets are welcome! A wonderful combination of space, comfort, community amenities, and a desirable location.

3 Beds ⋅ 3 Baths ⋅ 1064994 MLS

Welcome home to this spacious 3-bedroom, 2.5-bath townhouse-style home located in the highly sought-after Syosset School District! Ideally situated as a desirable corner unit on a quiet cul-de-sac, this home offers a bright and spacious layout with beautiful wood floors throughout the main living areas and carpeting only in the bedrooms. Features include Andersen windows throughout, central air, gas heat, a cozy fireplace, attached garage, and pull-down attic offering additional storage. Step outside to a beautiful brand-new private patio, perfect for relaxing or entertaining. Enjoy fantastic community amenities including a swimming pool, tennis courts, playground, and more. Pets are welcome! A wonderful combination of space, comfort, community amenities, and a desirable location.

23 Pond Path, Woodbury

$449,999

This move-in-ready, three-bedroom, two-bath ranch is located in Highland Mills within the Cornwall Central School District. The home offers approximately 1,408 square feet of main-level living space with a functional layout and inviting outdoor surroundings. A beautiful yard and surrounding woods create a peaceful setting for relaxing on the deck, gardening, or enjoying the outdoors. The full basement provides additional storage, while the one-car garage adds everyday convenience. Enjoy convenient access to shopping, dining, Hudson Valley hiking, and commuter routes to New York City. Eligible residents may also use Woodbury’s community pool and reservoir facilities for swimming, fishing, and other outdoor activities.

3 Beds ⋅ 2 Baths ⋅ 1063346 MLS

This move-in-ready, three-bedroom, two-bath ranch is located in Highland Mills within the Cornwall Central School District. The home offers approximately 1,408 square feet of main-level living space with a functional layout and inviting outdoor surroundings. A beautiful yard and surrounding woods create a peaceful setting for relaxing on the deck, gardening, or enjoying the outdoors. The full basement provides additional storage, while the one-car garage adds everyday convenience. Enjoy convenient access to shopping, dining, Hudson Valley hiking, and commuter routes to New York City. Eligible residents may also use Woodbury’s community pool and reservoir facilities for swimming, fishing, and other outdoor activities.

30 Elmwood Drive, Woodbury

$649,900

Welcome to this stunning, fully remodeled Colonial in Woodbury, located in beautiful Litchfield County! Situated on over 2 acres with a private pond, this home features 4 bedrooms, 2 full baths, 2 half baths, a fully remodeled basement, central air, and a 2-car garage with low taxes! Some of the recent updates include a new roof, windows, doors, and mechanicals. Enjoy peaceful pond views from the screened-in porch. This exceptional property is waiting for its new owner!

4 Beds ⋅ 4 Baths ⋅ 24213335 MLS

Welcome to this stunning, fully remodeled Colonial in Woodbury, located in beautiful Litchfield County! Situated on over 2 acres with a private pond, this home features 4 bedrooms, 2 full baths, 2 half baths, a fully remodeled basement, central air, and a 2-car garage with low taxes! Some of the recent updates include a new roof, windows, doors, and mechanicals. Enjoy peaceful pond views from the screened-in porch. This exceptional property is waiting for its new owner!

67 Flanders Rd, Woodbury

$999,000

Welcome to this charming split-level home nestled in the heart of Woodbury, located in the Syosset School District. Situated on an oversized 85'x150' lot, property offers plenty of space for entertaining, relaxing, and enjoying outdoor living. The beautifully established grounds feature mature specimen plantings adding privacy, character and natural beauty to the property. The home features 3 spacious bedrooms, 2.5 baths, and hardwood flooring throughout all bedrooms. A large den provides additional space for gatherings and everyday living. The 2-car garage offers ample parking and storage. Additional highlights include a gas heating system and a newer roof. Ideally located on a dead-end street within a cul-de-sac, this home offers both privacy and convenience. Enjoy close proximity to shopping, school, houses of worship and other local amenities. A wonderful opportunity to own a spacious home on a beautiful oversized property in desirable Woodbury location within the Syosset School District.

3 Beds ⋅ 3 Baths ⋅ 1044983 MLS

Welcome to this charming split-level home nestled in the heart of Woodbury, located in the Syosset School District. Situated on an oversized 85'x150' lot, property offers plenty of space for entertaining, relaxing, and enjoying outdoor living. The beautifully established grounds feature mature specimen plantings adding privacy, character and natural beauty to the property. The home features 3 spacious bedrooms, 2.5 baths, and hardwood flooring throughout all bedrooms. A large den provides additional space for gatherings and everyday living. The 2-car garage offers ample parking and storage. Additional highlights include a gas heating system and a newer roof. Ideally located on a dead-end street within a cul-de-sac, this home offers both privacy and convenience. Enjoy close proximity to shopping, school, houses of worship and other local amenities. A wonderful opportunity to own a spacious home on a beautiful oversized property in desirable Woodbury location within the Syosset School District.

20 Canterbury Road, Woodbury

$529,000

Looking for a convenient in town location? Built in 1940, this delightful vintage colonial is loaded with the charm of the 1940's. The front to back living room offers a fireplace, built ins as well as oak flooring. It also features a French door to the rear porch overlooking the spacious rear yard. Located adjacent to the kitchen, the formal dining room features a built-in china closet and oak flooring. A powder room and laundry area complete the main level. Upstairs, a front to back primary bedroom with oak flooring. There are two bedrooms and a full bath on this level. Need more room? The walk-up attic is floored provides the opportunity for future expansion. There is a rec room on the lower level for additional space.

3 Beds ⋅ 2 Baths ⋅ 24210084 MLS

Looking for a convenient in town location? Built in 1940, this delightful vintage colonial is loaded with the charm of the 1940's. The front to back living room offers a fireplace, built ins as well as oak flooring. It also features a French door to the rear porch overlooking the spacious rear yard. Located adjacent to the kitchen, the formal dining room features a built-in china closet and oak flooring. A powder room and laundry area complete the main level. Upstairs, a front to back primary bedroom with oak flooring. There are two bedrooms and a full bath on this level. Need more room? The walk-up attic is floored provides the opportunity for future expansion. There is a rec room on the lower level for additional space.

11 Judson Ave, Woodbury

$699,900

Completely renovated and move-in ready, this three-bedroom ranch in North Woodbury has been gutted to the studs and beautifully rebuilt throughout. The open-concept layout features a gorgeous new kitchen with center island opening to a spacious family and dining area with plenty of room for larger gatherings. No detail was overlooked in the renovation. All three bedrooms feature hardwood floors, while the home also offers a new full bath, new laundry room, and a private side deck just off the entry. The finished lower level provides valuable additional living space for a family room, home office, exercise area, or recreation room. A rare opportunity to own a like-new ranch-style home in Woodbury with nothing left to do but move in and enjoy.

3 Beds ⋅ 2 Baths ⋅ 24211238 MLS

Completely renovated and move-in ready, this three-bedroom ranch in North Woodbury has been gutted to the studs and beautifully rebuilt throughout. The open-concept layout features a gorgeous new kitchen with center island opening to a spacious family and dining area with plenty of room for larger gatherings. No detail was overlooked in the renovation. All three bedrooms feature hardwood floors, while the home also offers a new full bath, new laundry room, and a private side deck just off the entry. The finished lower level provides valuable additional living space for a family room, home office, exercise area, or recreation room. A rare opportunity to own a like-new ranch-style home in Woodbury with nothing left to do but move in and enjoy.

1217 Main St N, Woodbury

$330,000

Welcome to 1108 Evergreen Court in Woodbury! This desirable end-unit condo offers added privacy and a great location next to the community pool. Enter through the foyer before heading upstairs to the main living area, where you’ll find a bright and inviting layout. The living room opens to a private deck, providing a great spot to relax and enjoy the outdoors. The galley-style kitchen offers convenient seating and opens to a separate dining area, perfect for everyday meals or entertaining. A detached garage with electric provides additional parking and storage, plus there is plenty of unassigned parking for residents and guests. Enjoy low-maintenance living with community amenities and convenient access to shopping, dining, recreation, and major roadways. With its end-unit location, deck, garage, ample parking, and proximity to the pool, 1108 Evergreen Court has plenty to offer!

2 Beds ⋅ 2 Baths ⋅ 1056467 MLS

Welcome to 1108 Evergreen Court in Woodbury! This desirable end-unit condo offers added privacy and a great location next to the community pool. Enter through the foyer before heading upstairs to the main living area, where you’ll find a bright and inviting layout. The living room opens to a private deck, providing a great spot to relax and enjoy the outdoors. The galley-style kitchen offers convenient seating and opens to a separate dining area, perfect for everyday meals or entertaining. A detached garage with electric provides additional parking and storage, plus there is plenty of unassigned parking for residents and guests. Enjoy low-maintenance living with community amenities and convenient access to shopping, dining, recreation, and major roadways. With its end-unit location, deck, garage, ample parking, and proximity to the pool, 1108 Evergreen Court has plenty to offer!

1108 Evergreen Court Unit #65, Woodbury

$290,000

Rare opportunity in desirable Woodbury Village! This charming three-level townhouse offers flexible living space, beautiful natural light, and a peaceful setting in the heart of Woodbury. The main level welcomes you with a spacious living room featuring a large bay window and abundant natural light. The adjoining eat-in kitchen offers generous pantry storage and sliders leading to a private deck overlooking a lovely wooded green space-the perfect spot for morning coffee or relaxing outdoors. A convenient half bath with laundry and additional storage completes this level. Upstairs, you'll find two generously sized bedrooms with ample closet space, including a walk-in closet, along with a full bath and additional linen storage. The finished walk-out lower level adds valuable bonus space and offers endless possibilities as a home office, recreation room, guest space, gym, or additional living area. Sliding doors open to a covered outdoor area and backyard space. The basement has also been waterproofed and features newer carpeting. Additional features include space for a private garden, three portable air-conditioning units (one with heat), a basement dehumidifier, and deck furniture included by the seller. Woodbury Village offers a tranquil setting with expansive green space, mature trees, walking areas, and a river running through the complex-all while being conveniently located just minutes from Woodbury's shops, restaurants, and everyday amenities.

2 Beds ⋅ 2 Baths ⋅ 24210496 MLS ⋅ Woodbury Village BLDG.

Rare opportunity in desirable Woodbury Village! This charming three-level townhouse offers flexible living space, beautiful natural light, and a peaceful setting in the heart of Woodbury. The main level welcomes you with a spacious living room featuring a large bay window and abundant natural light. The adjoining eat-in kitchen offers generous pantry storage and sliders leading to a private deck overlooking a lovely wooded green space-the perfect spot for morning coffee or relaxing outdoors. A convenient half bath with laundry and additional storage completes this level. Upstairs, you'll find two generously sized bedrooms with ample closet space, including a walk-in closet, along with a full bath and additional linen storage. The finished walk-out lower level adds valuable bonus space and offers endless possibilities as a home office, recreation room, guest space, gym, or additional living area. Sliding doors open to a covered outdoor area and backyard space. The basement has also been waterproofed and features newer carpeting. Additional features include space for a private garden, three portable air-conditioning units (one with heat), a basement dehumidifier, and deck furniture included by the seller. Woodbury Village offers a tranquil setting with expansive green space, mature trees, walking areas, and a river running through the complex-all while being conveniently located just minutes from Woodbury's shops, restaurants, and everyday amenities.

74 Washington Road Unit 40, Woodbury

$950,000

A private retreat with Million dollar views! Nestled at the end of a peaceful cul-de-sac, this 3800+ Colonial offers a rare combination of privacy, space, and breathtaking views. Set against a backdrop of rolling hills, with gorgeous sunsets - where every season brings a beautiful new view. Step inside and you'll be greeted by expansive LR/Great RM featuring soaring cathedral ceilings, freshly painted walls, and an abundance of natural light. Kitchen is appointed with granite countertops, SS appliances, double pantries, double sinks and a wine chiller making it functional and inviting. Rich Brazilian Cherry HW floors add warmth and elegance throughout the first floor. The first floor primary suite offers a peaceful retreat of its own, highlighted by a claw-foot soaking tub to relax while taking in the views. Upstairs, three additional bedrooms, along with a renovated full bathroom featuring marble walk-in shower and marble countertops. A cozy area(den) for family time and dedicated office space. Lets not forget the bonus living space above the garage. This separate entrance living space includes two-bedroom, kitchen, LR, laundry and garage space. The possibilities for extended family, guests, au pair, rental income or Airbnb option are endless.

6 Beds ⋅ 4 Baths ⋅ 24209295 MLS

A private retreat with Million dollar views! Nestled at the end of a peaceful cul-de-sac, this 3800+ Colonial offers a rare combination of privacy, space, and breathtaking views. Set against a backdrop of rolling hills, with gorgeous sunsets - where every season brings a beautiful new view. Step inside and you'll be greeted by expansive LR/Great RM featuring soaring cathedral ceilings, freshly painted walls, and an abundance of natural light. Kitchen is appointed with granite countertops, SS appliances, double pantries, double sinks and a wine chiller making it functional and inviting. Rich Brazilian Cherry HW floors add warmth and elegance throughout the first floor. The first floor primary suite offers a peaceful retreat of its own, highlighted by a claw-foot soaking tub to relax while taking in the views. Upstairs, three additional bedrooms, along with a renovated full bathroom featuring marble walk-in shower and marble countertops. A cozy area(den) for family time and dedicated office space. Lets not forget the bonus living space above the garage. This separate entrance living space includes two-bedroom, kitchen, LR, laundry and garage space. The possibilities for extended family, guests, au pair, rental income or Airbnb option are endless.

92 Quail Run Rd, Woodbury

$875,000

Welcome to history, charm, and an incredible location-the best of both worlds! Tucked along a quiet side road, this lovingly cared-for antique offers a peaceful, private setting with a picturesque waterfall nearby, yet is within walking distance to an amazing collection of local favorites, including fine restaurants, diners, a brewery, pub with live entertainment, and French bakery. No wonder they call it "Food-bury!" A stone path leads to a beautiful stone landing and a home filled with warmth and character. The spacious L-shaped living room offers two inviting gathering areas-one centered around a wood-burning fireplace with room for a grand piano, and the other warmed by a woodstove beside a full-wall library and second seating area. Just beyond is a sun-filled, beamed room wrapped in windows on three sides, perfect for breakfast, reading, art, TV, or simply enjoying the view. The charming country kitchen is exceptionally appointed with premium Viking, Miele, Sub-Zero, Dacor and Fisher & Paykel appliances, including an induction cooktop, wall and speed ovens, warming drawer and 2-drawer dishwasher. Thoughtful details include Waterworks fixtures, a pot filler, custom pull-out cabinetry and under-cabinet lighting. Two staircases lead to three restful bedrooms and two beautifully renovated full baths. The primary bath features a Waterworks vanity with quartz top and Waterworks hardware, while the second bath creates a spa-like retreat with a soaking tub and steam shower.

3 Beds ⋅ 3 Baths ⋅ 24209527 MLS

Welcome to history, charm, and an incredible location-the best of both worlds! Tucked along a quiet side road, this lovingly cared-for antique offers a peaceful, private setting with a picturesque waterfall nearby, yet is within walking distance to an amazing collection of local favorites, including fine restaurants, diners, a brewery, pub with live entertainment, and French bakery. No wonder they call it "Food-bury!" A stone path leads to a beautiful stone landing and a home filled with warmth and character. The spacious L-shaped living room offers two inviting gathering areas-one centered around a wood-burning fireplace with room for a grand piano, and the other warmed by a woodstove beside a full-wall library and second seating area. Just beyond is a sun-filled, beamed room wrapped in windows on three sides, perfect for breakfast, reading, art, TV, or simply enjoying the view. The charming country kitchen is exceptionally appointed with premium Viking, Miele, Sub-Zero, Dacor and Fisher & Paykel appliances, including an induction cooktop, wall and speed ovens, warming drawer and 2-drawer dishwasher. Thoughtful details include Waterworks fixtures, a pot filler, custom pull-out cabinetry and under-cabinet lighting. Two staircases lead to three restful bedrooms and two beautifully renovated full baths. The primary bath features a Waterworks vanity with quartz top and Waterworks hardware, while the second bath creates a spa-like retreat with a soaking tub and steam shower.

2 Pomperaug Rd, Woodbury

$199,900

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

2 Beds ⋅ 1 Baths ⋅ 24209657 MLS ⋅ Town In Country BLDG.

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

229 Bacon Pond Rd Unit 312, Woodbury

$849,900

Reader's Digest named Woodbury the "Most Charming Small Town in Connecticut" in 2024 and received the same recognition in 2020 and 2018.That fits this home perfectly. 63 Main St N is an 1850 antique home with a 2002 addition, offering 4 bedrooms, 2 updated bathrooms and 2,662 square feet of delight on 0.36 acres. It has the historic character people expect from Main Street - mahogany-floored wrap-around porch, oak floors, built-ins and fireplaces - while also having an open kitchen/dining/family-room layout, gas log fireplace, first-floor bedroom, updated bath and attached garage. The backyard should be another major focus. It has beautiful stone walls, an outdoor fireplace, new 43" outdoor gas grill, hot tub, irrigation system and a completely flat yard with room for entertaining and potentially a future pool.

4 Beds ⋅ 2 Baths ⋅ 24208978 MLS

Reader's Digest named Woodbury the "Most Charming Small Town in Connecticut" in 2024 and received the same recognition in 2020 and 2018.That fits this home perfectly. 63 Main St N is an 1850 antique home with a 2002 addition, offering 4 bedrooms, 2 updated bathrooms and 2,662 square feet of delight on 0.36 acres. It has the historic character people expect from Main Street - mahogany-floored wrap-around porch, oak floors, built-ins and fireplaces - while also having an open kitchen/dining/family-room layout, gas log fireplace, first-floor bedroom, updated bath and attached garage. The backyard should be another major focus. It has beautiful stone walls, an outdoor fireplace, new 43" outdoor gas grill, hot tub, irrigation system and a completely flat yard with room for entertaining and potentially a future pool.

63 Main St N, Woodbury

$899,000

Welcome to 2 Woodtree Drive at The Woodlands. This turnkey, DIAMOND-condition, 3-bedroom, 2.5-bathroom home awaits. This corner unit, gut-renovated in 2018, features top-of-the-line finishes, custom millwork, and a bright, open layout while maintaining a cozy feel throughout. Upon entry, you'll find a beautiful kitchen with stainless steel Bosch appliances, wooden cabinetry, and a bright double slider to the patio. The laundry area is conveniently located between the kitchen and the generously sized den/living room, with an adjacent dining room. This level also features a tastefully appointed half bathroom. Upstairs, the primary bed and bath are generously sized, with two additional bedrooms and one additional bathroom. Additionally, it has reverse osmosis drinking water, a full-house filtration system, and a Nest thermostat. This is easy living at its finest, with amenities including a clubhouse, tennis courts, a pool, and beautiful grounds. Minutes from trails and nature paths. Extremely close to the LIRR at both Cold Spring Harbor and Syosset stations. Syosset School District. **Parking lot is the first right when you come into The Woodlands - Park in any of the spots**

3 Beds ⋅ 3 Baths ⋅ 1054251 MLS

Welcome to 2 Woodtree Drive at The Woodlands. This turnkey, DIAMOND-condition, 3-bedroom, 2.5-bathroom home awaits. This corner unit, gut-renovated in 2018, features top-of-the-line finishes, custom millwork, and a bright, open layout while maintaining a cozy feel throughout. Upon entry, you'll find a beautiful kitchen with stainless steel Bosch appliances, wooden cabinetry, and a bright double slider to the patio. The laundry area is conveniently located between the kitchen and the generously sized den/living room, with an adjacent dining room. This level also features a tastefully appointed half bathroom. Upstairs, the primary bed and bath are generously sized, with two additional bedrooms and one additional bathroom. Additionally, it has reverse osmosis drinking water, a full-house filtration system, and a Nest thermostat. This is easy living at its finest, with amenities including a clubhouse, tennis courts, a pool, and beautiful grounds. Minutes from trails and nature paths. Extremely close to the LIRR at both Cold Spring Harbor and Syosset stations. Syosset School District. **Parking lot is the first right when you come into The Woodlands - Park in any of the spots**

2 Woodtree Drive, Woodbury

$294,900

Welcome to 47 Woods Way! This beautifully renovated Woodlake townhouse is truly move-in ready, offering stylish updates and the convenience of a garage just steps from your front door. Step inside to discover a gorgeous new kitchen featuring crisp white Shaker cabinetry, gleaming quartz countertops, and stainless steel appliances. New RevWood by Mohawk flooring flows throughout the first floor, complemented by a charming shiplap-accented fireplace that creates a warm and inviting focal point in the living room. Upstairs, the spacious primary suite offers a beautifully renovated ensuite bathroom, creating a private retreat at the end of the day. Enjoy a brand-new tiled shower with niche, modern vanity and tasteful finishes. The guest bathroom has also been thoughtfully updated with new porcelain tile flooring, oak vanity, new lighting, and mirror. Plush new wall-to-wall carpeting throughout the second floor lends a cozy, fresh feel to the bedrooms. A brand new hot water heater, and a two year old HVAC system add comfort and peace of mind. The amenities continue with a garage featuring a new door opener, plus a full unfinished basement offering excellent storage and flexibility. A newer washer and dryer and a private sun deck off the living room round out the package. With its fresh renovations, thoughtful updates, and convenient location, 47 Woods Way offers the perfect blend of style, comfort, and easy living. Just unpack and enjoy!

2 Beds ⋅ 2 Baths ⋅ 24209304 MLS ⋅ Woodlake BLDG.

Welcome to 47 Woods Way! This beautifully renovated Woodlake townhouse is truly move-in ready, offering stylish updates and the convenience of a garage just steps from your front door. Step inside to discover a gorgeous new kitchen featuring crisp white Shaker cabinetry, gleaming quartz countertops, and stainless steel appliances. New RevWood by Mohawk flooring flows throughout the first floor, complemented by a charming shiplap-accented fireplace that creates a warm and inviting focal point in the living room. Upstairs, the spacious primary suite offers a beautifully renovated ensuite bathroom, creating a private retreat at the end of the day. Enjoy a brand-new tiled shower with niche, modern vanity and tasteful finishes. The guest bathroom has also been thoughtfully updated with new porcelain tile flooring, oak vanity, new lighting, and mirror. Plush new wall-to-wall carpeting throughout the second floor lends a cozy, fresh feel to the bedrooms. A brand new hot water heater, and a two year old HVAC system add comfort and peace of mind. The amenities continue with a garage featuring a new door opener, plus a full unfinished basement offering excellent storage and flexibility. A newer washer and dryer and a private sun deck off the living room round out the package. With its fresh renovations, thoughtful updates, and convenient location, 47 Woods Way offers the perfect blend of style, comfort, and easy living. Just unpack and enjoy!

47 Woods Way Unit 47, Woodbury

$550,000

Charming Brick Ranch on 2+ Acres Nestled on more than two acres in a peaceful setting, this well-built brick ranch offers the perfect blend of privacy, comfort, and convenience, with easy access to shopping, dining, and everyday amenities. The home has been freshly painted, meticulously maintained, and reflects pride of ownership throughout. Inside, you'll find a spacious and inviting floor plan featuring hardwood flooring in the living room and all three bedrooms, adding warmth and character to the main living spaces. The kitchen and pantry are finished with durable vinyl flooring, providing easy care and everyday practicality. The generously sized kitchen features ample counter space, a pantry, a cozy eating area, and a gas fireplace, making it an ideal gathering place for family and friends. The living room is enhanced by built-in bookcases, while the bedrooms offer hardwood floors and built-in desks, combining charm with functionality. The primary bedroom includes a private full bath, creating a comfortable retreat. Additional highlights include a lower-level room, a workshop with walkout access, a tandem garage with room for vehicles and storage, and a fully insulated walk-up attic offering exciting possibilities for future expansion, hobbies, or additional storage. If you're looking for a solidly constructed home with acreage, character, and room to grow, this property presents a rare opportunity to enjoy country-style tranquility without sacrificing convenien

3 Beds ⋅ 2 Baths ⋅ 24206868 MLS

Charming Brick Ranch on 2+ Acres Nestled on more than two acres in a peaceful setting, this well-built brick ranch offers the perfect blend of privacy, comfort, and convenience, with easy access to shopping, dining, and everyday amenities. The home has been freshly painted, meticulously maintained, and reflects pride of ownership throughout. Inside, you'll find a spacious and inviting floor plan featuring hardwood flooring in the living room and all three bedrooms, adding warmth and character to the main living spaces. The kitchen and pantry are finished with durable vinyl flooring, providing easy care and everyday practicality. The generously sized kitchen features ample counter space, a pantry, a cozy eating area, and a gas fireplace, making it an ideal gathering place for family and friends. The living room is enhanced by built-in bookcases, while the bedrooms offer hardwood floors and built-in desks, combining charm with functionality. The primary bedroom includes a private full bath, creating a comfortable retreat. Additional highlights include a lower-level room, a workshop with walkout access, a tandem garage with room for vehicles and storage, and a fully insulated walk-up attic offering exciting possibilities for future expansion, hobbies, or additional storage. If you're looking for a solidly constructed home with acreage, character, and room to grow, this property presents a rare opportunity to enjoy country-style tranquility without sacrificing convenien

578 Old Sherman Hill Rd, Woodbury

$850,000

A Place Where Home Feels Like A Getaway Welcome to 69 Nonnewaug Road, where peaceful country living meets the charm of Woodbury! Set on approximately 9.47 acres, this 3-bedroom, 3-bath home offers an incredible combination of space, privacy, and outdoor living. Surrounded by beautiful natural scenery, the expansive property provides plenty of room to spread out, explore, garden, entertain, or simply enjoy the peaceful setting. Spend warm summer days relaxing by the pool, host gatherings with family and friends, or unwind and take in the privacy of your own country retreat. Inside, the home offers a comfortable and inviting layout with three bedrooms and three full baths, providing plenty of space for everyday living and guests. But the lifestyle extends well beyond the walls-with nearly 10 acres and your own pool, there's plenty of opportunity to enjoy the property throughout the seasons. Located in the charming town of Woodbury, known for its quintessential New England character, historic appeal, local shops, restaurants, and picturesque countryside, this home offers a wonderful balance of privacy and convenience. If you've been dreaming of more land, more privacy, and a place where home feels like a getaway, 69 Nonnewaug Road is one you won't want to miss!

4 Beds ⋅ 3 Baths ⋅ 24208716 MLS

A Place Where Home Feels Like A Getaway Welcome to 69 Nonnewaug Road, where peaceful country living meets the charm of Woodbury! Set on approximately 9.47 acres, this 3-bedroom, 3-bath home offers an incredible combination of space, privacy, and outdoor living. Surrounded by beautiful natural scenery, the expansive property provides plenty of room to spread out, explore, garden, entertain, or simply enjoy the peaceful setting. Spend warm summer days relaxing by the pool, host gatherings with family and friends, or unwind and take in the privacy of your own country retreat. Inside, the home offers a comfortable and inviting layout with three bedrooms and three full baths, providing plenty of space for everyday living and guests. But the lifestyle extends well beyond the walls-with nearly 10 acres and your own pool, there's plenty of opportunity to enjoy the property throughout the seasons. Located in the charming town of Woodbury, known for its quintessential New England character, historic appeal, local shops, restaurants, and picturesque countryside, this home offers a wonderful balance of privacy and convenience. If you've been dreaming of more land, more privacy, and a place where home feels like a getaway, 69 Nonnewaug Road is one you won't want to miss!

69 Nonnewaug Rd, Woodbury

$274,900

Welcome home to Woodlake! The Woodlake community provides non-motorized boating on the lake, hiking trails, basketball, tennis courts, and a playground area for the kids to name a few. This end unit is within a short walking distance of the lake, clubhouse and other complex amenities! Spacious and bright, this Congeniality II model offers an open floor plan, and two spacious bedrooms with 2.5 baths. Freshly painted, this unit's kitchen offers newer cabinets, appliances and fixtures. The expansive combination living and dining room features hardwood floors and ample space to host the upcoming holidays! Off the living room, step out onto the back deck to grill and enjoy seasonal views of the lake. The main level is finished off by an updated half bath. The upper level offers two generously sized bedrooms, including two full bathrooms. The primary-suite features laminate flooring, plenty of closet space, and stall shower. The second level full bath has newer vanity, granite countertops and custom built-in. Newer carpet lines the stairs down to the mostly finished basement. This space provides another option for livable space, or additional room for play or work including a private patio. Both sliders have been recently replaced. This well-maintained community provides a responsive, on-site property management company. Live in Woodbury for under 300k with no exterior maintenance demands! Woodlake is in close proximity of Woodbury and Southbury town centers!

2 Beds ⋅ 3 Baths ⋅ 24206920 MLS ⋅ Woodlake BLDG.

Welcome home to Woodlake! The Woodlake community provides non-motorized boating on the lake, hiking trails, basketball, tennis courts, and a playground area for the kids to name a few. This end unit is within a short walking distance of the lake, clubhouse and other complex amenities! Spacious and bright, this Congeniality II model offers an open floor plan, and two spacious bedrooms with 2.5 baths. Freshly painted, this unit's kitchen offers newer cabinets, appliances and fixtures. The expansive combination living and dining room features hardwood floors and ample space to host the upcoming holidays! Off the living room, step out onto the back deck to grill and enjoy seasonal views of the lake. The main level is finished off by an updated half bath. The upper level offers two generously sized bedrooms, including two full bathrooms. The primary-suite features laminate flooring, plenty of closet space, and stall shower. The second level full bath has newer vanity, granite countertops and custom built-in. Newer carpet lines the stairs down to the mostly finished basement. This space provides another option for livable space, or additional room for play or work including a private patio. Both sliders have been recently replaced. This well-maintained community provides a responsive, on-site property management company. Live in Woodbury for under 300k with no exterior maintenance demands! Woodlake is in close proximity of Woodbury and Southbury town centers!

3 Shagbark Ln Unit 3, Woodbury

$289,000

Woodlake has 7 Ranch Style Units with either a carport or garage; making #5 Alder Court is a rare-find-end unit! The walk from the parking area is level to an inviting Court-yard and onto this lovely ranch style home. You will notice the natural private surroundings. Once inside, beautiful wood floors greet you. Beautiful windows provide natural sunlight. The LR has a cathedral ceiling. The Fireplace, (one of two) has been sealed shut for safety. Woodlake will allow wood-burning or pellet stove inserts with permits. The Woodlake Office can assist with the paperwork. The galley kitchen has new granite tops. The Primary Bedroom is ensuite. There is ample storage and closets in both bedrooms. The Walk-out Lower Level is finished with newer vinyl flooring. There is a laundry room with set-sink. Included are two working washing machines, (The small washer was used for baby clothes) a dryer and set-sink.the ping-pong table can be yours if you wish! The quintessential Town of Woodbury was recently voted The Best small Town in CT by Readers Digest and the Boston Globe. It's an easy commute east or west to I84. There are two Town Greens, and restaurants to delight every palate. There are parks to enjoy, trails to hike, garden, performing arts and learning centers. Explore Boutiques, Antiques and visit the Woodbury portion of the CT Wine Trail! This is a beautiful time of Year at Woodlake and in Woodbury CT! Visit soon!

2 Beds ⋅ 2 Baths ⋅ 24205782 MLS ⋅ Woodlake BLDG.

Woodlake has 7 Ranch Style Units with either a carport or garage; making #5 Alder Court is a rare-find-end unit! The walk from the parking area is level to an inviting Court-yard and onto this lovely ranch style home. You will notice the natural private surroundings. Once inside, beautiful wood floors greet you. Beautiful windows provide natural sunlight. The LR has a cathedral ceiling. The Fireplace, (one of two) has been sealed shut for safety. Woodlake will allow wood-burning or pellet stove inserts with permits. The Woodlake Office can assist with the paperwork. The galley kitchen has new granite tops. The Primary Bedroom is ensuite. There is ample storage and closets in both bedrooms. The Walk-out Lower Level is finished with newer vinyl flooring. There is a laundry room with set-sink. Included are two working washing machines, (The small washer was used for baby clothes) a dryer and set-sink.the ping-pong table can be yours if you wish! The quintessential Town of Woodbury was recently voted The Best small Town in CT by Readers Digest and the Boston Globe. It's an easy commute east or west to I84. There are two Town Greens, and restaurants to delight every palate. There are parks to enjoy, trails to hike, garden, performing arts and learning centers. Explore Boutiques, Antiques and visit the Woodbury portion of the CT Wine Trail! This is a beautiful time of Year at Woodlake and in Woodbury CT! Visit soon!

5 Alder Ct Unit 84A, Woodbury

$599,900

The John Cramer House at 10 Weekeepeemee Road is listed on the National Register of Historic Places and is a wonderful example of Greek Revival architecture. Rich in period character, the home features beautiful chestnut plank flooring, nearly 9-foot ceilings, and an original fireplace with a beehive oven. The first floor offers a study, living room, dining room, granite-countered kitchen, and a charming breakfast room with wood stove and half bath. Upstairs are three bedrooms, a full bath with marble counter, and conveniently located laundry. A full walk-up attic leads to a large finished space with additional storage and closet space. An attached shed provides a potting area and stairs to a second-floor loft. Set on 3.09 acres, the property also includes a historic barn with a two-car garage, two horse stalls, and a full second floor. Open field and wooded areas create a peaceful country setting, with elevated views toward the town of Woodbury from the upper portion of the property. Across the road, enjoy seasonal views of the Weekeepeemee River, adding to the charm and character of this special historic property.

3 Beds ⋅ 2 Baths ⋅ 24207451 MLS

The John Cramer House at 10 Weekeepeemee Road is listed on the National Register of Historic Places and is a wonderful example of Greek Revival architecture. Rich in period character, the home features beautiful chestnut plank flooring, nearly 9-foot ceilings, and an original fireplace with a beehive oven. The first floor offers a study, living room, dining room, granite-countered kitchen, and a charming breakfast room with wood stove and half bath. Upstairs are three bedrooms, a full bath with marble counter, and conveniently located laundry. A full walk-up attic leads to a large finished space with additional storage and closet space. An attached shed provides a potting area and stairs to a second-floor loft. Set on 3.09 acres, the property also includes a historic barn with a two-car garage, two horse stalls, and a full second floor. Open field and wooded areas create a peaceful country setting, with elevated views toward the town of Woodbury from the upper portion of the property. Across the road, enjoy seasonal views of the Weekeepeemee River, adding to the charm and character of this special historic property.

10 Weekeepeemee Rd, Woodbury

$209,900

Move right into this beautifully renovated upper end unit in Woodbury's desirable in-town Town & Country condominium complex. Tastefully updated throughout, this light-filled unit features an open floor plan with a completely renovated kitchen flowing into the living room with fireplace and built-ins. Updates include new windows, luxury vinyl plank flooring, interior doors, lighting, switches, outlets, and electrical finishes throughout. Ideally located toward the rear of the complex, the unit overlooks the pool and landscaped grounds, offering a peaceful setting with added privacy. One of the standout units in the complex, this turnkey property combines quality updates, an excellent location, and the convenience of being within walking distance to shops, restaurants, and everything historic Woodbury has to offer.

2 Beds ⋅ 1 Baths ⋅ 24206004 MLS ⋅ Town In Country BLDG.

Move right into this beautifully renovated upper end unit in Woodbury's desirable in-town Town & Country condominium complex. Tastefully updated throughout, this light-filled unit features an open floor plan with a completely renovated kitchen flowing into the living room with fireplace and built-ins. Updates include new windows, luxury vinyl plank flooring, interior doors, lighting, switches, outlets, and electrical finishes throughout. Ideally located toward the rear of the complex, the unit overlooks the pool and landscaped grounds, offering a peaceful setting with added privacy. One of the standout units in the complex, this turnkey property combines quality updates, an excellent location, and the convenience of being within walking distance to shops, restaurants, and everything historic Woodbury has to offer.

229 Bacon Pond Rd Unit 313, Woodbury

$765,000

Newly re-imagined and completely renovated single level jewel box on quiet country lane with tree-lined driveway and long seasonal views. The open-concept living areas are designed for effortless entertaining with soaring vaulted ceilings, exposed beams, a floor-to-ceiling brick double-sided fireplace and a fabulous dedicated bar room. A new series of skylights creates a bright and airy space filled with all day sunlight. Eat-in chef's kitchen features bespoke cabinetry and premium appliances. A delightful 3-season dining/living porch with wood stove leads to an expansive stone patio overlooking the large level lawn. Stunning primary suite with vaulted ceiling and beams has a large walk-in closet and a gorgeous bathroom with double sinks and over-sized shower. The second bedroom is served by a handsome full hall bath. Convenient mud and laundry room. All new mechanicals, roof and shingle siding. Detached 2-car garage. Be the first to own this mint condition home peacefully nestled in the sought-after Flanders section of the quintessential New England town of Woodbury. Perfection!

2 Beds ⋅ 2 Baths ⋅ 24203113 MLS

Newly re-imagined and completely renovated single level jewel box on quiet country lane with tree-lined driveway and long seasonal views. The open-concept living areas are designed for effortless entertaining with soaring vaulted ceilings, exposed beams, a floor-to-ceiling brick double-sided fireplace and a fabulous dedicated bar room. A new series of skylights creates a bright and airy space filled with all day sunlight. Eat-in chef's kitchen features bespoke cabinetry and premium appliances. A delightful 3-season dining/living porch with wood stove leads to an expansive stone patio overlooking the large level lawn. Stunning primary suite with vaulted ceiling and beams has a large walk-in closet and a gorgeous bathroom with double sinks and over-sized shower. The second bedroom is served by a handsome full hall bath. Convenient mud and laundry room. All new mechanicals, roof and shingle siding. Detached 2-car garage. Be the first to own this mint condition home peacefully nestled in the sought-after Flanders section of the quintessential New England town of Woodbury. Perfection!

31 Bethwood Ln, Woodbury

$679,900

Imagine starting your morning with a cup of coffee on the gorgeous wraparound front porch as you take in the view of Radey Pond or spending warm summer evenings entertaining family and friends in this beautiful and private setting.Situated on 2.31 acres, this charming 3/4-bedroom, 2.5-bath Cape/Colonial offers the perfect combination of classic New England character, comfortable living space, and a flexible floor plan. At the heart of the home is the spacious eat-in kitchen, offering plenty of counter and cabinet space and flowing naturally into the inviting family room with a cozy fireplace. Whether you're entertaining a crowd or enjoying a quiet evening at home, this warm and welcoming space is made for gathering.A separate living room and office/den provide additional options for relaxing, working from home, or creating a space that fits your lifestyle.Upstairs, the spacious primary suite is a true retreat with a large closet and private full bath featuring a spa tub and separate shower. Two additional generously sized bedrooms share another well-appointed full bathroom.Need even more room? The finished third floor offers wonderful flexibility and can easily become a fourth bedroom, private home office. Hardwood floors throughout add timeless appeal, while a new roof offers peace of mind.Outside, the 2.31-acre private lot and beautiful pond views create a setting that feels removed from it all, while still being conveniently located near amenities, and major highways

3 Beds ⋅ 3 Baths ⋅ 24204212 MLS

Imagine starting your morning with a cup of coffee on the gorgeous wraparound front porch as you take in the view of Radey Pond or spending warm summer evenings entertaining family and friends in this beautiful and private setting.Situated on 2.31 acres, this charming 3/4-bedroom, 2.5-bath Cape/Colonial offers the perfect combination of classic New England character, comfortable living space, and a flexible floor plan. At the heart of the home is the spacious eat-in kitchen, offering plenty of counter and cabinet space and flowing naturally into the inviting family room with a cozy fireplace. Whether you're entertaining a crowd or enjoying a quiet evening at home, this warm and welcoming space is made for gathering.A separate living room and office/den provide additional options for relaxing, working from home, or creating a space that fits your lifestyle.Upstairs, the spacious primary suite is a true retreat with a large closet and private full bath featuring a spa tub and separate shower. Two additional generously sized bedrooms share another well-appointed full bathroom.Need even more room? The finished third floor offers wonderful flexibility and can easily become a fourth bedroom, private home office. Hardwood floors throughout add timeless appeal, while a new roof offers peace of mind.Outside, the 2.31-acre private lot and beautiful pond views create a setting that feels removed from it all, while still being conveniently located near amenities, and major highways

201 Transylvania Rd, Woodbury

$675,000

Some homes make their impression at the front door. This one begins long before it. Set nearly out of sight on almost three acres, the home is approached by a long driveway that opens to a circular drive and generous garage parking, a gracious arrival that feels worlds away. Inside, the floor plan delivers more than expected: a sunlit living room, formal dining room, updated white kitchen with breakfast space, and a generous family room anchored by a dramatic stone fireplace. Upstairs are three bedrooms and two full baths, while the finished walkout lower level adds a recreation room, flex room, and dedicated laundry space that can shift with the way you live. The outdoor experience is equally considered, with three distinct places to gather: a welcoming front patio, elevated rear deck, and lower-level patio leading toward the in-ground pool. Framed by bluestone, open lawn, and mature woods, the pool feels less like an amenity and more like a private summer destination. Yet this retreat is only minutes from Woodbury's Main Street celebrated for its restaurants, local shops, and antiques and close to trails and open space at Minortown Road Preserve and Orenaug Park. Private without being remote, flexible without feeling ordinary, this is a home designed for quiet mornings, effortless entertaining, and unforgettable weekends.

3 Beds ⋅ 3 Baths ⋅ 24200785 MLS

Some homes make their impression at the front door. This one begins long before it. Set nearly out of sight on almost three acres, the home is approached by a long driveway that opens to a circular drive and generous garage parking, a gracious arrival that feels worlds away. Inside, the floor plan delivers more than expected: a sunlit living room, formal dining room, updated white kitchen with breakfast space, and a generous family room anchored by a dramatic stone fireplace. Upstairs are three bedrooms and two full baths, while the finished walkout lower level adds a recreation room, flex room, and dedicated laundry space that can shift with the way you live. The outdoor experience is equally considered, with three distinct places to gather: a welcoming front patio, elevated rear deck, and lower-level patio leading toward the in-ground pool. Framed by bluestone, open lawn, and mature woods, the pool feels less like an amenity and more like a private summer destination. Yet this retreat is only minutes from Woodbury's Main Street celebrated for its restaurants, local shops, and antiques and close to trails and open space at Minortown Road Preserve and Orenaug Park. Private without being remote, flexible without feeling ordinary, this is a home designed for quiet mornings, effortless entertaining, and unforgettable weekends.

61 Minortown Rd, Woodbury

$420,000

Welcome to 34 Pilgrim Trail, a home thoughtfully cared for and enjoyed for 25.5 years. This peaceful Woodbury property features granite kitchen countertops, a tiled backsplash, stainless-steel appliances, and a ceramic kitchen floor. Solid pine doors throughout the home add warmth and character. The upstairs bathroom has been beautifully updated, including the tub and a solid-rock vanity countertop. The upper bedroom/closet offers flexible use and can easily be converted back to a bedroom. Additional improvements include updated closet systems, a refreshed closet near the upstairs bathroom, and a roof installed in 2011. The home is generator-ready, with the generator located outside. Enjoy the tranquility of the property while remaining just minutes from Main Street, shopping, and New Morning Market. Nearby schools and everyday conveniences make this a wonderful place to call home.

4 Beds ⋅ 2 Baths ⋅ 24203216 MLS

Welcome to 34 Pilgrim Trail, a home thoughtfully cared for and enjoyed for 25.5 years. This peaceful Woodbury property features granite kitchen countertops, a tiled backsplash, stainless-steel appliances, and a ceramic kitchen floor. Solid pine doors throughout the home add warmth and character. The upstairs bathroom has been beautifully updated, including the tub and a solid-rock vanity countertop. The upper bedroom/closet offers flexible use and can easily be converted back to a bedroom. Additional improvements include updated closet systems, a refreshed closet near the upstairs bathroom, and a roof installed in 2011. The home is generator-ready, with the generator located outside. Enjoy the tranquility of the property while remaining just minutes from Main Street, shopping, and New Morning Market. Nearby schools and everyday conveniences make this a wonderful place to call home.

34 Pilgrim Trl, Woodbury

$825,000

Original owner, large Colonial Home with 4 room, private entry inlaw suite on the main level. Close to town center and schools. With all this s/footage it's price at an unheard of $197. per! Bring on the big multi-generational family! Natural sun filtered house has front and back staircases, large rooms, 9'ceilings, and mostly hardwood. Granite kitchen/ great room open to breakfast nook, family room w fireplace and french doors to rear decking. Formal dining room and living room are a must in this classic style. The entertaining space is oversized so host all the holiday gatherings with ease. Primary suite is HUGE, walk in plus another closet and luxury bath. 3 additional bedrooms and an office. A separate 2nd floor laundry room, also very generous in size. Very level usable yard with a large area off the back deck fenced for dogs. (used to have a pool). Brand new central AC unit, refinished hardwood and fresh paint on the main level. In-law apartment is propane heat/ac

5 Beds ⋅ 4 Baths ⋅ 24200842 MLS

Original owner, large Colonial Home with 4 room, private entry inlaw suite on the main level. Close to town center and schools. With all this s/footage it's price at an unheard of $197. per! Bring on the big multi-generational family! Natural sun filtered house has front and back staircases, large rooms, 9'ceilings, and mostly hardwood. Granite kitchen/ great room open to breakfast nook, family room w fireplace and french doors to rear decking. Formal dining room and living room are a must in this classic style. The entertaining space is oversized so host all the holiday gatherings with ease. Primary suite is HUGE, walk in plus another closet and luxury bath. 3 additional bedrooms and an office. A separate 2nd floor laundry room, also very generous in size. Very level usable yard with a large area off the back deck fenced for dogs. (used to have a pool). Brand new central AC unit, refinished hardwood and fresh paint on the main level. In-law apartment is propane heat/ac

132 Good Hill Rd, Woodbury

$699,000

Classic 1930s Colonial set along Main Street in Woodbury, offering the timeless character and craftsmanship of the era. Thoughtfully set back from the road on an expansive lawn, the home features hardwood floors throughout, high ceilings, detailed moldings, interior French doors, charming built-ins, a generous foyer, and a graceful central staircase. The front-to-back living room is anchored by a brick fireplace and opens to a spacious covered porch, creating an inviting setting for everyday living and entertaining. The kitchen and both bathrooms have been updated, blending modern convenience with the home's original character. A beautiful 34' x 27' post-and-beam barn provides exceptional space for a workshop, studio, storage, or other uses. Located within Woodbury's Main Street Design District, the property also offers the flexibility to combine residential living with a business use, subject to applicable regulations. A distinctive property with room to live, work, and enjoy the best of classic Woodbury.

4 Beds ⋅ 2 Baths ⋅ 24194243 MLS

Classic 1930s Colonial set along Main Street in Woodbury, offering the timeless character and craftsmanship of the era. Thoughtfully set back from the road on an expansive lawn, the home features hardwood floors throughout, high ceilings, detailed moldings, interior French doors, charming built-ins, a generous foyer, and a graceful central staircase. The front-to-back living room is anchored by a brick fireplace and opens to a spacious covered porch, creating an inviting setting for everyday living and entertaining. The kitchen and both bathrooms have been updated, blending modern convenience with the home's original character. A beautiful 34' x 27' post-and-beam barn provides exceptional space for a workshop, studio, storage, or other uses. Located within Woodbury's Main Street Design District, the property also offers the flexibility to combine residential living with a business use, subject to applicable regulations. A distinctive property with room to live, work, and enjoy the best of classic Woodbury.

126 Main St N, Woodbury

$999,000

Welcome to this beautifully renovated and meticulously maintained condo in the heart of the prestigious Woodlands community. This impressive residence offers an open, airy layout with quality finishes and a fresh, modern feel throughout. The spacious eat-in kitchen features custom cabinetry, stainless steel appliances, quartz countertops, porcelain flooring and a center island that opens to the formal dining area - perfect for both everyday living and entertaining. The beautifully appointed primary suite offers a private en-suite bath and spacious walk-in closet. With three bathrooms in total, including two full baths, the home provides a thoughtful and functional layout. Additional highlights include hardwood floors, vaulted ceilings, skylights and a finished basement, providing additional living and recreational space. Enjoy the exceptional country club lifestyle The Woodlands has to offer, including a pool, tennis, pickleball, fitness room, playground and clubhouse. A wonderful opportunity to enjoy a beautifully appointed home, outstanding community amenities and an exceptional Woodbury location, Syosset Schools

3 Beds ⋅ 3 Baths ⋅ 1037907 MLS

Welcome to this beautifully renovated and meticulously maintained condo in the heart of the prestigious Woodlands community. This impressive residence offers an open, airy layout with quality finishes and a fresh, modern feel throughout. The spacious eat-in kitchen features custom cabinetry, stainless steel appliances, quartz countertops, porcelain flooring and a center island that opens to the formal dining area - perfect for both everyday living and entertaining. The beautifully appointed primary suite offers a private en-suite bath and spacious walk-in closet. With three bathrooms in total, including two full baths, the home provides a thoughtful and functional layout. Additional highlights include hardwood floors, vaulted ceilings, skylights and a finished basement, providing additional living and recreational space. Enjoy the exceptional country club lifestyle The Woodlands has to offer, including a pool, tennis, pickleball, fitness room, playground and clubhouse. A wonderful opportunity to enjoy a beautifully appointed home, outstanding community amenities and an exceptional Woodbury location, Syosset Schools

115 Woody Lane, Woodbury

$749,900

Impressive and spacious 5,815 sq. ft. well maintained residence with BRAND NEW ROOF and all new skylight windows(installed 8/15/26) offering exceptional one-level living with 6 bedrooms, 4 full bathrooms, and an oversized heated 3-car garage. A welcoming 12' x 9' slate-floor foyer introduces the home and leads to generously proportioned living spaces designed for both everyday comfort and entertaining. The oversized formal dining room provides an impressive setting for large gatherings, while the well-appointed kitchen features granite countertops, a casual eat-in area, double Viking ovens, a Viking 6-burner cooktop, and Miele dishwasher. Two fireplaces add warmth and character throughout the home, while a whole-house sound system enhances both indoor and outdoor entertaining. The expansive 37' x 23' heated three-car garage offers abundant room for vehicles, storage, hobbies, or workshop space, feel secure with a whole house generator. Outdoors, enjoy a large slate patio entertainment area complete with a wood-fired grill, overlooking a spacious, level yard with plenty of room for recreation and gatherings. With six bedrooms, expansive living areas, quality amenities, and the convenience of true one-level living, this distinctive Woodbury property offers an exceptional combination of space, comfort, and versatility.

6 Beds ⋅ 4 Baths ⋅ 24187148 MLS

Impressive and spacious 5,815 sq. ft. well maintained residence with BRAND NEW ROOF and all new skylight windows(installed 8/15/26) offering exceptional one-level living with 6 bedrooms, 4 full bathrooms, and an oversized heated 3-car garage. A welcoming 12' x 9' slate-floor foyer introduces the home and leads to generously proportioned living spaces designed for both everyday comfort and entertaining. The oversized formal dining room provides an impressive setting for large gatherings, while the well-appointed kitchen features granite countertops, a casual eat-in area, double Viking ovens, a Viking 6-burner cooktop, and Miele dishwasher. Two fireplaces add warmth and character throughout the home, while a whole-house sound system enhances both indoor and outdoor entertaining. The expansive 37' x 23' heated three-car garage offers abundant room for vehicles, storage, hobbies, or workshop space, feel secure with a whole house generator. Outdoors, enjoy a large slate patio entertainment area complete with a wood-fired grill, overlooking a spacious, level yard with plenty of room for recreation and gatherings. With six bedrooms, expansive living areas, quality amenities, and the convenience of true one-level living, this distinctive Woodbury property offers an exceptional combination of space, comfort, and versatility.

24 Scuppo Rd, Woodbury

$510,000

Welcome to beautiful Woodbury, CT! Beautiful 2 BR, 2 1/2 bath condo in sought after Woodbury Hill Condos. Park like grounds with only 78 condos, featuring a saltwater pool and a tennis/pickleball court. Well maintained condo features the main level with a Living room with vaulted ceiling and a wood-burning fireplace, dining room w/bow window, a half bath with granite vanity, an updated kitchen w/granite counters and an eating area. Sliders lead out to an oversized private deck with awning and a fantastic view! Primary BR on main level w/full updated bath w/marble vanity, walk-in closet, and an additional slider that leads out to the deck, complete with stairs down to back yard. Upper level features an interior balcony that overlooks the living room below, has a loft and a generous sized 2nd bedroom w/walk-in closet. Lots of closets space and walk in attic eve storage as well. This level also has a full bathroom with granite vanity. Lower level features a large family room with built-ins and walk out slider to the back yard, a separate play room and a large laundry room w/slop sink. Recent updates include, new LG French Door refrigerator (3/26), new hot water heater (2025), new water pump (2025). Exterior home and deck freshly painted June/July 2026. Don't miss seeing this one!

2 Beds ⋅ 3 Baths ⋅ 24188214 MLS ⋅ Woodbury Hill BLDG.

Welcome to beautiful Woodbury, CT! Beautiful 2 BR, 2 1/2 bath condo in sought after Woodbury Hill Condos. Park like grounds with only 78 condos, featuring a saltwater pool and a tennis/pickleball court. Well maintained condo features the main level with a Living room with vaulted ceiling and a wood-burning fireplace, dining room w/bow window, a half bath with granite vanity, an updated kitchen w/granite counters and an eating area. Sliders lead out to an oversized private deck with awning and a fantastic view! Primary BR on main level w/full updated bath w/marble vanity, walk-in closet, and an additional slider that leads out to the deck, complete with stairs down to back yard. Upper level features an interior balcony that overlooks the living room below, has a loft and a generous sized 2nd bedroom w/walk-in closet. Lots of closets space and walk in attic eve storage as well. This level also has a full bathroom with granite vanity. Lower level features a large family room with built-ins and walk out slider to the back yard, a separate play room and a large laundry room w/slop sink. Recent updates include, new LG French Door refrigerator (3/26), new hot water heater (2025), new water pump (2025). Exterior home and deck freshly painted June/July 2026. Don't miss seeing this one!

35 Woodbury Hill, Unit 35, Woodbury

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