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Tucked away in a private and peaceful setting, this beautifully appointed Colonial offers an exceptional blend of comfort, style and functionality. Hardwood floors and custom millwork are showcased throughout, creating a warm and refined atmosphere. A dramatic two-story foyer welcomes you and is flanked by a first-floor office with transom-topped French doors for privacy. Opposite, a double opening with a transom window leads to the formal dining room, which flows seamlessly into the formal living room-ideal for entertaining. The spacious eat-in kitchen is thoughtfully designed with stainless steel appliances, granite countertops, a center island, and a dining area with sliders leading to a large patio-perfect for effortless indoor-outdoor living and entertaining. The kitchen opens to a generous family room featuring a fireplace and custom built-in bookcases, creating a comfortable and inviting gathering space. A half bath and convenient mudroom complete the main level. Upstairs, the home offers four bedrooms, all with wall-to-wall carpeting, including a spacious primary suite with tray ceiling and a full bath with double vanities, a soaking tub, and a walk-in shower. A dedicated laundry room enhances everyday convenience. The unfinished lower level provides excellent potential for future living space, allowing the next owner to tailor it to their needs. Enjoy a large, level yard ideal for recreation, gardening or gatherings.. Your peaceful retreat awaits!

4 Beds ⋅ 3 Baths ⋅ 24138603 MLS

Tucked away in a private and peaceful setting, this beautifully appointed Colonial offers an exceptional blend of comfort, style and functionality. Hardwood floors and custom millwork are showcased throughout, creating a warm and refined atmosphere. A dramatic two-story foyer welcomes you and is flanked by a first-floor office with transom-topped French doors for privacy. Opposite, a double opening with a transom window leads to the formal dining room, which flows seamlessly into the formal living room-ideal for entertaining. The spacious eat-in kitchen is thoughtfully designed with stainless steel appliances, granite countertops, a center island, and a dining area with sliders leading to a large patio-perfect for effortless indoor-outdoor living and entertaining. The kitchen opens to a generous family room featuring a fireplace and custom built-in bookcases, creating a comfortable and inviting gathering space. A half bath and convenient mudroom complete the main level. Upstairs, the home offers four bedrooms, all with wall-to-wall carpeting, including a spacious primary suite with tray ceiling and a full bath with double vanities, a soaking tub, and a walk-in shower. A dedicated laundry room enhances everyday convenience. The unfinished lower level provides excellent potential for future living space, allowing the next owner to tailor it to their needs. Enjoy a large, level yard ideal for recreation, gardening or gatherings.. Your peaceful retreat awaits!

99 Plumb Brook Rd, Woodbury

$850,000

Welcome to Woodbury! Rebuilt in 1991, this stunning 3,736 sq ft single-family estate sits gracefully on over 11 acres, offering the perfect blend of refined luxury and serene countryside living. Step inside to discover a spacious, light-filled interior designed for both grand entertaining and comfortable everyday living. With four generously sized bedrooms, multiple living areas, and fine architectural details throughout, every corner of this home exudes sophistication. The gourmet kitchen opens to elegant dining and family spaces, while expansive windows frame picturesque views of the surrounding landscape. Outdoors, a built-in pool invites you to relax and entertain in style, with plenty of room to expand your vision - whether it's a garden, horse paddock, additional dwelling or private vineyard. A three-car garage and circular driveway ensure privacy and convenience, all within minutes of Woodbury's charming town center, fine dining, and schools. This is more than a home - it's an estate, a retreat, and a lifestyle.

4 Beds ⋅ 3 Baths ⋅ 24086901 MLS

Welcome to Woodbury! Rebuilt in 1991, this stunning 3,736 sq ft single-family estate sits gracefully on over 11 acres, offering the perfect blend of refined luxury and serene countryside living. Step inside to discover a spacious, light-filled interior designed for both grand entertaining and comfortable everyday living. With four generously sized bedrooms, multiple living areas, and fine architectural details throughout, every corner of this home exudes sophistication. The gourmet kitchen opens to elegant dining and family spaces, while expansive windows frame picturesque views of the surrounding landscape. Outdoors, a built-in pool invites you to relax and entertain in style, with plenty of room to expand your vision - whether it's a garden, horse paddock, additional dwelling or private vineyard. A three-car garage and circular driveway ensure privacy and convenience, all within minutes of Woodbury's charming town center, fine dining, and schools. This is more than a home - it's an estate, a retreat, and a lifestyle.

84 Hurds Hill Rd, Woodbury

$839,000

This meticulously maintained and beloved Colonial home in a beautiful community sits on an oversized 1.2 acre landscaped lot, offering privacy and views from its expansive oversized windows, the trex deck and stone inlaid patio! Enjoy almost 3,000 sqft. of finished space with a full basement that can also be completed having the plumbing for an additional bathroom in place and sliding glass doors that lead to the spacious stone patio. The paved driveway has plenty of parking for visitors and the two car garage with additional storage leads you into the home; next to the laundry room, half bath, walk in pantry and eat-in kitchen for easy transport of groceries. The kitchen is a chef's dream, having an abundance of counter space, an island, and even a dry bar that connects to a formal dining room. Off of the dining area of the kitchen is a set of sliding glass doors that lead to an updated trex deck with stairs to the patio and tree lined backyard. The living room is light and airy with two-story high ceiling and a wall of windows as well as a wood burning fireplace. A cozy family room completes the main level. Upon entering the front door, your senses are delighted by the natural light from the many windows, openness of the floor plan and view of the second floor hallway. The second floor features a capacious primary bedroom with a high ceiling, two walk-in closets, a double sink bathroom with a walk-in shower and a separate tub. There is another full bath shared among the other three sizable bedrooms. One of which also has a walk-in closet. The hallway opens up to overlook the bright living room and foyer continuing to delight the sense of integrated space and flow of this charming home. The community features a clubhouse, in-ground pool, tennis courts and playground; just a short stroll or drive away. Affordable 98.00 monthly HOA includes the maintenance of these enjoyable spaces, as well as recycling and refuse removal. Municipal water and sewer add to the peace of mind of low maintenance and quality living. About an hour to NYC!

4 Beds ⋅ 3 Baths ⋅ 874343 MLS

This meticulously maintained and beloved Colonial home in a beautiful community sits on an oversized 1.2 acre landscaped lot, offering privacy and views from its expansive oversized windows, the trex deck and stone inlaid patio! Enjoy almost 3,000 sqft. of finished space with a full basement that can also be completed having the plumbing for an additional bathroom in place and sliding glass doors that lead to the spacious stone patio. The paved driveway has plenty of parking for visitors and the two car garage with additional storage leads you into the home; next to the laundry room, half bath, walk in pantry and eat-in kitchen for easy transport of groceries. The kitchen is a chef's dream, having an abundance of counter space, an island, and even a dry bar that connects to a formal dining room. Off of the dining area of the kitchen is a set of sliding glass doors that lead to an updated trex deck with stairs to the patio and tree lined backyard. The living room is light and airy with two-story high ceiling and a wall of windows as well as a wood burning fireplace. A cozy family room completes the main level. Upon entering the front door, your senses are delighted by the natural light from the many windows, openness of the floor plan and view of the second floor hallway. The second floor features a capacious primary bedroom with a high ceiling, two walk-in closets, a double sink bathroom with a walk-in shower and a separate tub. There is another full bath shared among the other three sizable bedrooms. One of which also has a walk-in closet. The hallway opens up to overlook the bright living room and foyer continuing to delight the sense of integrated space and flow of this charming home. The community features a clubhouse, in-ground pool, tennis courts and playground; just a short stroll or drive away. Affordable 98.00 monthly HOA includes the maintenance of these enjoyable spaces, as well as recycling and refuse removal. Municipal water and sewer add to the peace of mind of low maintenance and quality living. About an hour to NYC!

10 Heather Ridge, Woodbury

$835,000

Calling all Snowbirds!! 242 Coach Drive is an exquisite 2-bedroom, 2-bathroom condo spanning 1,100 sq. ft. in the prestigious Kensington Estates, a 24-hour gated boutique community in Woodbury NY, designed for a luxurious, low-maintenance lifestyle for residents 55 and over. This exceptional unit is one of the few benefiting from a rare tax abatement for the next 7.5 years. Current annual property taxes are under $1,800- making this home an extraordinary value for luxury living. This single-story residence boasts 9-foot ceilings with elegant crown molding and base moldings throughout, creating a refined and spacious ambiance. Step into a bright, open concept living space with expansive windows that flood the home with natural light, seamlessly connecting the living room, dining area, and gourmet kitchen, perfect for both intimate gatherings and entertainment. Beautiful chef’s kitchen, featuring a premium Wolf range, Sub-Zero refrigerator, sleek stainless-steel appliances, custom cabinetry, and stunning quartz countertops, ideal for culinary enthusiasts. The serene primary suite offers a generous walk-in closet with custom shelving and a spa-inspired en-suite bathroom adorned with upgraded Carrera marble, premium Kohler fixtures, and modern LED mirrors for a touch of luxury. The elegant second bedroom, accompanied by a full bathroom with matching Carrera marble, Kohler fixtures, and LED mirrors, provides flexibility for guests, a home office, or a cozy den. Rich, wide-plank oak flooring runs throughout, adding warmth and timeless elegance. Outside, a beautifully crafted covered Nicolock paver patio with plenty of room for furniture and a BBQ overlooks a gorgeous grassy open space with a western exposure and beautiful sunsets , creating a tranquil setting for al fresco dining or relaxation. The home is equipped with state-of-the-art systems, including a Navien tankless hot water heater, natural gas heating, central air conditioning with smart thermostats, a fire suppression sprinkler system, and an advanced alarm system for safety and comfort. A high-efficiency LG washer and dryer are tucked away in a dedicated laundry closet, and municipal sewer connections ensure hassle-free, eco-friendly living Nestled within 18 acres of impeccably landscaped grounds, Kensington Estates offers resort-like amenities, including a sparkling pool, tennis courts, a state-of-the-art fitness center, a private clubhouse for social events, and scenic walking paths around a tranquil pond. Perfectly situated near the charming villages of Cold Spring Harbor, Huntington, and Syosset, this condo provides easy access to boutique shopping, fine dining, cultural attractions and major highways, blending suburban serenity with urban convenience. Located within the renowned Syosset School District, this home offers access to top-tier education, adding to its appeal. This home is a rare opportunity, especially with its exceptionally low property taxes and turnkey condition. Don't wait on this one!

2 Beds ⋅ 2 Baths ⋅ 906859 MLS

Calling all Snowbirds!! 242 Coach Drive is an exquisite 2-bedroom, 2-bathroom condo spanning 1,100 sq. ft. in the prestigious Kensington Estates, a 24-hour gated boutique community in Woodbury NY, designed for a luxurious, low-maintenance lifestyle for residents 55 and over. This exceptional unit is one of the few benefiting from a rare tax abatement for the next 7.5 years. Current annual property taxes are under $1,800- making this home an extraordinary value for luxury living. This single-story residence boasts 9-foot ceilings with elegant crown molding and base moldings throughout, creating a refined and spacious ambiance. Step into a bright, open concept living space with expansive windows that flood the home with natural light, seamlessly connecting the living room, dining area, and gourmet kitchen, perfect for both intimate gatherings and entertainment. Beautiful chef’s kitchen, featuring a premium Wolf range, Sub-Zero refrigerator, sleek stainless-steel appliances, custom cabinetry, and stunning quartz countertops, ideal for culinary enthusiasts. The serene primary suite offers a generous walk-in closet with custom shelving and a spa-inspired en-suite bathroom adorned with upgraded Carrera marble, premium Kohler fixtures, and modern LED mirrors for a touch of luxury. The elegant second bedroom, accompanied by a full bathroom with matching Carrera marble, Kohler fixtures, and LED mirrors, provides flexibility for guests, a home office, or a cozy den. Rich, wide-plank oak flooring runs throughout, adding warmth and timeless elegance. Outside, a beautifully crafted covered Nicolock paver patio with plenty of room for furniture and a BBQ overlooks a gorgeous grassy open space with a western exposure and beautiful sunsets , creating a tranquil setting for al fresco dining or relaxation. The home is equipped with state-of-the-art systems, including a Navien tankless hot water heater, natural gas heating, central air conditioning with smart thermostats, a fire suppression sprinkler system, and an advanced alarm system for safety and comfort. A high-efficiency LG washer and dryer are tucked away in a dedicated laundry closet, and municipal sewer connections ensure hassle-free, eco-friendly living Nestled within 18 acres of impeccably landscaped grounds, Kensington Estates offers resort-like amenities, including a sparkling pool, tennis courts, a state-of-the-art fitness center, a private clubhouse for social events, and scenic walking paths around a tranquil pond. Perfectly situated near the charming villages of Cold Spring Harbor, Huntington, and Syosset, this condo provides easy access to boutique shopping, fine dining, cultural attractions and major highways, blending suburban serenity with urban convenience. Located within the renowned Syosset School District, this home offers access to top-tier education, adding to its appeal. This home is a rare opportunity, especially with its exceptionally low property taxes and turnkey condition. Don't wait on this one!

242 Coach Drive, Woodbury

$825,000

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

3 Beds ⋅ 3 Baths ⋅ 24192675 MLS

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

17 Curtiss Rd, Woodbury

$825,000

PRICE IMPROVEMENT !!!! Own an Iconic Connecticut Restaurant. This family run restaurant and adjacent residence has been under the same ownership since the 1950s. This turnkey operation offers great potential to continue current operations or a new culinary vision. Generations of Success, over 70 years in operation, built on community trust and steady clientele. Well-appointed kitchen, dining area, and full-service facilities. NDA and Proof of funds Required: Confidential information available upon signing. Don't miss this unique chance to own a time-tested restaurant and property combo. Reach out today.

2 Baths ⋅ 24105595 MLS

PRICE IMPROVEMENT !!!! Own an Iconic Connecticut Restaurant. This family run restaurant and adjacent residence has been under the same ownership since the 1950s. This turnkey operation offers great potential to continue current operations or a new culinary vision. Generations of Success, over 70 years in operation, built on community trust and steady clientele. Well-appointed kitchen, dining area, and full-service facilities. NDA and Proof of funds Required: Confidential information available upon signing. Don't miss this unique chance to own a time-tested restaurant and property combo. Reach out today.

670 Main St N, Woodbury

$820,000

Welcome to this beautifully maintained condo located in the highly sought-after Woodlands community in Woodbury. Offering the perfect blend of comfort, space, and convenience, this 3-bedroom, 2.5-bath home is designed for both everyday living and effortless entertaining!! The main level features a generously sized bedroom and bathroom that provide flexibility for guests or a home office! Enjoy meals in the eat-in kitchen or host gatherings in the formal dining room! Additional highlights include a washer and dryer, abundant closet space, and access to a full basement complete with a cozy fireplace—ideal for a recreation room or additional living space! A bright and inviting living room is complemented by natural light and high ceilings that enhance the home’s airy feel!! Upstairs, you’ll find two well-appointed bedrooms, including a spacious primary suite with its own en-suite bathroom, walk-in closets, and excellent storage! An additional full bathroom serves the second bedroom, offering comfort and privacy for all!! Sliding glass doors lead to your own private backyard area—perfect for relaxing or entertaining guests in a peaceful setting! Residents of The Woodlands enjoy a private, resort-style lifestyle with exceptional amenities, including an in-ground pool, tennis and pickleball courts, a playground, clubhouse with lounge, card room, fitness center, and meeting spaces!! Don’t miss the opportunity to make this bright, spacious, and amenity-rich home your own!!!

3 Beds ⋅ 3 Baths ⋅ 975866 MLS

Welcome to this beautifully maintained condo located in the highly sought-after Woodlands community in Woodbury. Offering the perfect blend of comfort, space, and convenience, this 3-bedroom, 2.5-bath home is designed for both everyday living and effortless entertaining!! The main level features a generously sized bedroom and bathroom that provide flexibility for guests or a home office! Enjoy meals in the eat-in kitchen or host gatherings in the formal dining room! Additional highlights include a washer and dryer, abundant closet space, and access to a full basement complete with a cozy fireplace—ideal for a recreation room or additional living space! A bright and inviting living room is complemented by natural light and high ceilings that enhance the home’s airy feel!! Upstairs, you’ll find two well-appointed bedrooms, including a spacious primary suite with its own en-suite bathroom, walk-in closets, and excellent storage! An additional full bathroom serves the second bedroom, offering comfort and privacy for all!! Sliding glass doors lead to your own private backyard area—perfect for relaxing or entertaining guests in a peaceful setting! Residents of The Woodlands enjoy a private, resort-style lifestyle with exceptional amenities, including an in-ground pool, tennis and pickleball courts, a playground, clubhouse with lounge, card room, fitness center, and meeting spaces!! Don’t miss the opportunity to make this bright, spacious, and amenity-rich home your own!!!

37 Aspen Drive W Unit #37, Woodbury

$810,000

Country Living Abounds with this unique custom built one of a kind Cape nestled on 5 secluded acres. This home features an open floor plan with post and beam construction, beamed ceilings, oak floors, Plaster Walls, fully applianced Kitchen with breakfast bar, a spacious Family Room with brick fireplace, built-ins, & slider leading to back deck. The Living Room with fireplace is adjacent to a spacious Dining Room area & slider leading to large deck with access to side yard. Enjoy some quiet time in the cozy Library with fireplace and built-ins. First floor also has an Office as well as a full Bathroom. As you ascend the stairs to the second floor you will marvel at the unique lighted brick archway. Second floor boasts of a lovely Primary Bedroom Suite with brick fireplace & raised hearth, walk-in closets, Full Bath with tub, shower & vanities, and slider leading to balcony, and Two other large Bedrooms with skylights, Full hallway Bathroom, & Laundry Room with utility sink. With In-law/apartment the total living space is 3882 sqft. This home is convenient to Woodbury's town center, shops, top restaurants, antiquing, and recreation with hiking trails & nearby lake. This property has so much to offer!

3 Beds ⋅ 4 Baths ⋅ 24149131 MLS

Country Living Abounds with this unique custom built one of a kind Cape nestled on 5 secluded acres. This home features an open floor plan with post and beam construction, beamed ceilings, oak floors, Plaster Walls, fully applianced Kitchen with breakfast bar, a spacious Family Room with brick fireplace, built-ins, & slider leading to back deck. The Living Room with fireplace is adjacent to a spacious Dining Room area & slider leading to large deck with access to side yard. Enjoy some quiet time in the cozy Library with fireplace and built-ins. First floor also has an Office as well as a full Bathroom. As you ascend the stairs to the second floor you will marvel at the unique lighted brick archway. Second floor boasts of a lovely Primary Bedroom Suite with brick fireplace & raised hearth, walk-in closets, Full Bath with tub, shower & vanities, and slider leading to balcony, and Two other large Bedrooms with skylights, Full hallway Bathroom, & Laundry Room with utility sink. With In-law/apartment the total living space is 3882 sqft. This home is convenient to Woodbury's town center, shops, top restaurants, antiquing, and recreation with hiking trails & nearby lake. This property has so much to offer!

148 Flanders Rd, Woodbury

$800,000

Welcome to a rare opportunity in the highly sought-after Woodlands community! This 3-bedroom, 2.5-bath townhouse offers space, light, and potential in a prime Syosset location within the top-rated Syosset School District, serving Baylis Elementary and H.B. Thompson Middle School. Offered in original condition, this home presents a rare opportunity to bring your vision to life and create a space tailored to your personal style. With great bones, a spacious layout, and abundant natural light, the potential is undeniable. The main level features an airy, open floor plan with soaring ceilings in the living room and sliding glass doors in both the living room and dining room leading to a private deck—ideal for seamless indoor-outdoor living and entertaining. A formal dining room and generously sized eat-in kitchen provide flexibility for both everyday living and hosting. The kitchen also offers direct access from the garage and includes a convenient laundry area. A standout feature is the expanded den, a versatile finished space offering additional living area that was converted by the Sponsor when the community was built. A conveniently located half bath completes this level. Upstairs, the home offers a primary en-suite with a large walk-in closet, two well-proportioned bedrooms, and a full hall bath. A spacious landing and hallway overlook the living room below, enhancing the home’s open and airy feel. The basement adds even more versatility, perfect for a recreation room, home office, gym, or additional storage. Additional highlights include a new HVAC system, an attached garage, and a private driveway with side-by-side parking for two vehicles. Enjoy resort-style living in this highly sought-after, amenity-rich pet-friendly community featuring tennis, pickleball, and basketball courts, a fitness center, clubhouse with social spaces, in-ground pool, kiddie pool, and playground. Conveniently located just minutes from shopping, dining, major highways, and the Town of Oyster Bay Golf Course. Bring your imagination and unlock the full potential of this exceptional home!

3 Beds ⋅ 3 Baths ⋅ 990054 MLS

Welcome to a rare opportunity in the highly sought-after Woodlands community! This 3-bedroom, 2.5-bath townhouse offers space, light, and potential in a prime Syosset location within the top-rated Syosset School District, serving Baylis Elementary and H.B. Thompson Middle School. Offered in original condition, this home presents a rare opportunity to bring your vision to life and create a space tailored to your personal style. With great bones, a spacious layout, and abundant natural light, the potential is undeniable. The main level features an airy, open floor plan with soaring ceilings in the living room and sliding glass doors in both the living room and dining room leading to a private deck—ideal for seamless indoor-outdoor living and entertaining. A formal dining room and generously sized eat-in kitchen provide flexibility for both everyday living and hosting. The kitchen also offers direct access from the garage and includes a convenient laundry area. A standout feature is the expanded den, a versatile finished space offering additional living area that was converted by the Sponsor when the community was built. A conveniently located half bath completes this level. Upstairs, the home offers a primary en-suite with a large walk-in closet, two well-proportioned bedrooms, and a full hall bath. A spacious landing and hallway overlook the living room below, enhancing the home’s open and airy feel. The basement adds even more versatility, perfect for a recreation room, home office, gym, or additional storage. Additional highlights include a new HVAC system, an attached garage, and a private driveway with side-by-side parking for two vehicles. Enjoy resort-style living in this highly sought-after, amenity-rich pet-friendly community featuring tennis, pickleball, and basketball courts, a fitness center, clubhouse with social spaces, in-ground pool, kiddie pool, and playground. Conveniently located just minutes from shopping, dining, major highways, and the Town of Oyster Bay Golf Course. Bring your imagination and unlock the full potential of this exceptional home!

29 Jennings Lane, Woodbury

$775,000

This Completely updated townhouse in the desirable Woodbury Village offers low-maintenance, stress free living and is convenient to all. The first floor features a floating hardwood floor throughout and a customized eat-in kitchen with abundant custom cabinetry with quartz counter tops, and stainless steel appliances. The open-concept dining room and living room area includes crown molding, a wood-burning fireplace with cultured-stone surround creating a warm and inviting space accented by a stylish feature wall. Upstairs are two spacious bedrooms, each with its own updated full bathroom. The primary bedroom offers two large closets and a skylight, and its bathroom includes a tub/shower combo with subway-tile walls. The second bedroom features an en-suite bath with a standing shower, porcelain-tile walls, and porcelain-tile floor. Additional storage is available in the pull-down attic in the hallway. Woodbury Village residents enjoy on-site amenities including a pool and tennis courts. There is truly nothing left to do but unpack—this home is a must-see! Price Improvement.

2 Beds ⋅ 3 Baths ⋅ 955733 MLS

This Completely updated townhouse in the desirable Woodbury Village offers low-maintenance, stress free living and is convenient to all. The first floor features a floating hardwood floor throughout and a customized eat-in kitchen with abundant custom cabinetry with quartz counter tops, and stainless steel appliances. The open-concept dining room and living room area includes crown molding, a wood-burning fireplace with cultured-stone surround creating a warm and inviting space accented by a stylish feature wall. Upstairs are two spacious bedrooms, each with its own updated full bathroom. The primary bedroom offers two large closets and a skylight, and its bathroom includes a tub/shower combo with subway-tile walls. The second bedroom features an en-suite bath with a standing shower, porcelain-tile walls, and porcelain-tile floor. Additional storage is available in the pull-down attic in the hallway. Woodbury Village residents enjoy on-site amenities including a pool and tennis courts. There is truly nothing left to do but unpack—this home is a must-see! Price Improvement.

6 Cold Harbour Lane, Woodbury

$775,000

Experience elevated New England living at 6 Strong Field Road, an exceptional 2024 custom-built Cape Cod residence set on a private, manicured 1-acre lot in one of Woodbury's most desirable enclaves. Designed for discerning buyers, this 4-bedroom, 2.5-bath masterpiece blends architectural sophistication with everyday comfort. Inside, you're welcomed by an airy open-concept floor plan, enhanced by dramatic vaulted ceilings, expansive windows, and finely crafted wide-plank hardwood flooring throughout. At the heart of the home is a designer gourmet kitchen-a showcase of form and function-featuring premium quartz countertops, custom cabinetry, a professional-grade appliance suite, and an oversized island perfect for hosting or gathering. The adjoining great room offers a warm, elegant atmosphere anchored by serene views and refined finishes. The first-floor primary suite is a luxurious retreat with a spa-style bath, dual vanities, walk-in glass shower, and a generous walk-in closet. A main level office is idle for work-from-home living. Upstairs, three additional bedrooms and a full bath accompany a spacious loft, perfect for a media lounge or reading retreat. Tucked at the end of a quiet cul-de-sac, just minutes from historic Woodbury's shops, dining, nature preserves, and top-rated schools, this home is a rare opportunity to enjoy elevated country living with modern convenience. Unmatched style, craftsmanship, and comfort-schedule your private showing at 6 Strong Field

4 Beds ⋅ 3 Baths ⋅ 24115107 MLS

Experience elevated New England living at 6 Strong Field Road, an exceptional 2024 custom-built Cape Cod residence set on a private, manicured 1-acre lot in one of Woodbury's most desirable enclaves. Designed for discerning buyers, this 4-bedroom, 2.5-bath masterpiece blends architectural sophistication with everyday comfort. Inside, you're welcomed by an airy open-concept floor plan, enhanced by dramatic vaulted ceilings, expansive windows, and finely crafted wide-plank hardwood flooring throughout. At the heart of the home is a designer gourmet kitchen-a showcase of form and function-featuring premium quartz countertops, custom cabinetry, a professional-grade appliance suite, and an oversized island perfect for hosting or gathering. The adjoining great room offers a warm, elegant atmosphere anchored by serene views and refined finishes. The first-floor primary suite is a luxurious retreat with a spa-style bath, dual vanities, walk-in glass shower, and a generous walk-in closet. A main level office is idle for work-from-home living. Upstairs, three additional bedrooms and a full bath accompany a spacious loft, perfect for a media lounge or reading retreat. Tucked at the end of a quiet cul-de-sac, just minutes from historic Woodbury's shops, dining, nature preserves, and top-rated schools, this home is a rare opportunity to enjoy elevated country living with modern convenience. Unmatched style, craftsmanship, and comfort-schedule your private showing at 6 Strong Field

6 Strong Field Rd, Woodbury

$770,000

Bright and inviting 2–3 bedroom condo with FULL FINISHED BASEMENT in desirable Woodbury, ideally located near highways, shops, and restaurants — and zoned for Award winning Syosset schools. This 1488 sq ft home offers a sun-filled living room with a cozy fireplace and sliding doors leading to a spacious deck, perfect for entertaining or relaxing outdoors. The eat-in kitchen provides comfortable daily living, while the den can be easily converted into a third bedroom for added flexibility. A major bonus is the fun, fully finished basement, ideal for a playroom, home gym, or media space — plus ample storage to keep everything organized. Enjoy community amenities including a pool and tennis / pickleball courts and a playground all within a convenient location close to major highways, shopping, restaurants, and everyday necessities. Perfect for anyone looking for space, comfort, and convenience in Woodbury.

3 Beds ⋅ 3 Baths ⋅ 947355 MLS

Bright and inviting 2–3 bedroom condo with FULL FINISHED BASEMENT in desirable Woodbury, ideally located near highways, shops, and restaurants — and zoned for Award winning Syosset schools. This 1488 sq ft home offers a sun-filled living room with a cozy fireplace and sliding doors leading to a spacious deck, perfect for entertaining or relaxing outdoors. The eat-in kitchen provides comfortable daily living, while the den can be easily converted into a third bedroom for added flexibility. A major bonus is the fun, fully finished basement, ideal for a playroom, home gym, or media space — plus ample storage to keep everything organized. Enjoy community amenities including a pool and tennis / pickleball courts and a playground all within a convenient location close to major highways, shopping, restaurants, and everyday necessities. Perfect for anyone looking for space, comfort, and convenience in Woodbury.

7 Village Lane, Woodbury

$765,000

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

4 Beds ⋅ 3 Baths ⋅ 24185801 MLS

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

62 Heritage Dr, Woodbury

$765,000

The Tomlinson House, built in 1783, offers a rare chance to own a piece of Woodbury's history. Set on 5+ acres along Middle Road Turnpike, with an additional .87-acres across the street, this 4-bedroom Colonial combines period charm with enduring potential. Historic character is evident throughout-restored wide-board hardwood floors, original millwork, and four (non-working) fireplaces, including a dramatic walk-in hearth with beehive oven. The floor plan provides the best of both worlds: a welcoming open flow between the kitchen and family room for gatherings around the hearth, balanced with dedicated dining and living rooms for more traditional entertaining. A main-level office/bedroom and screened porch add versatility. Upstairs, front and back staircases lead to three spacious bedrooms, two full baths, and a third-floor office with half bath. Recently refinished hardwood floors continue across the upper levels, preserving the home's warmth and continuity. The level property is a highlight...park-like and pastoral, with stone walls, a brook, pond, mature plantings, screened porch and a bluestone patio for outdoor living. A two-car garage with attached shed offers workshop or storage space. With strong bones, timeless appeal, and room to grow, the Tomlinson House is a unique offering in one of Woodbury's most desirable corridors

4 Beds ⋅ 4 Baths ⋅ 24123798 MLS

The Tomlinson House, built in 1783, offers a rare chance to own a piece of Woodbury's history. Set on 5+ acres along Middle Road Turnpike, with an additional .87-acres across the street, this 4-bedroom Colonial combines period charm with enduring potential. Historic character is evident throughout-restored wide-board hardwood floors, original millwork, and four (non-working) fireplaces, including a dramatic walk-in hearth with beehive oven. The floor plan provides the best of both worlds: a welcoming open flow between the kitchen and family room for gatherings around the hearth, balanced with dedicated dining and living rooms for more traditional entertaining. A main-level office/bedroom and screened porch add versatility. Upstairs, front and back staircases lead to three spacious bedrooms, two full baths, and a third-floor office with half bath. Recently refinished hardwood floors continue across the upper levels, preserving the home's warmth and continuity. The level property is a highlight...park-like and pastoral, with stone walls, a brook, pond, mature plantings, screened porch and a bluestone patio for outdoor living. A two-car garage with attached shed offers workshop or storage space. With strong bones, timeless appeal, and room to grow, the Tomlinson House is a unique offering in one of Woodbury's most desirable corridors

393 Middle Road Tpke, Woodbury

$750,000

Enjoy the Lifestyle of Woodbury Village, a sought after townhouse community in the Syosset School district offering exceptional amenities including a pool, tennis courts and playground. This 3 Bedroom(currently configured as 2 bedrooms plus a loft that can easily be converted back to 3rd bedroom), 2.5 Bath home features all New Flooring, New Primary Bathroom and Deck. The Main Level offers a Powder Room, an EIK with all SS Appliances, Granite Countertops and Abundant Cabinetry. The Sun filled Open Dining Room and Living Room is Ideal for Entertaining, Featuring a Striking Stone Fireplace and Sliding Glass Doors to the New Deck. Upstairs, the Spacious Primary Bedroom boasts 2 Closets and a Beautifully Renovated En-Suite Bath. A Second Bedroom, Versatile Loft/Bedroom, and a Full Bathroom complete the Second Level. Move Right in and enjoy comfortable, low maintenance living with resort style amenities in a prime location.

3 Beds ⋅ 3 Baths ⋅ 1013801 MLS

Enjoy the Lifestyle of Woodbury Village, a sought after townhouse community in the Syosset School district offering exceptional amenities including a pool, tennis courts and playground. This 3 Bedroom(currently configured as 2 bedrooms plus a loft that can easily be converted back to 3rd bedroom), 2.5 Bath home features all New Flooring, New Primary Bathroom and Deck. The Main Level offers a Powder Room, an EIK with all SS Appliances, Granite Countertops and Abundant Cabinetry. The Sun filled Open Dining Room and Living Room is Ideal for Entertaining, Featuring a Striking Stone Fireplace and Sliding Glass Doors to the New Deck. Upstairs, the Spacious Primary Bedroom boasts 2 Closets and a Beautifully Renovated En-Suite Bath. A Second Bedroom, Versatile Loft/Bedroom, and a Full Bathroom complete the Second Level. Move Right in and enjoy comfortable, low maintenance living with resort style amenities in a prime location.

5 Pond Path Unit #13, Woodbury

$750,000

HIGHEST & BEST OFFERS DUE BY NOON ON MONDAY, 4/13/26 - Fantastic opportunity to own this beautifully maintained 4-bedroom, 2.5-bath Colonial on lovely cul-de-sac neighborhood, privately set back on a wooded lot which backs up to Land Trust in sought-after Bear Run Estates. Proudly offered by its original owners, this home features numerous updates including a high-efficiency propane furnace (2023), central A/C (2024), and whole-house Generac generator (2023). A welcoming 2-story foyer leads to a fantastic eat-in kitchen with granite countertops, tiled backsplash, stainless steel appliances, breakfast bar, under-cabinet lighting, and pantry. The desirable open floor plan flows into the inviting family room with a propane fireplace and custom bookshelves. A private home office with a wall of built-ins, formal dining room, separate living room, and powder room with laundry complete the main level, all with beautiful hardwood flooring. Upstairs, the spacious primary bedroom suite offers exposed beams, walk-in closet, and renovated bath with soaking tub, tiled walk-in shower, and heated floors. Three additional generously sized bedrooms share a full bath. The walk-out lower level provides flexible finished space for a recreation room, gym, or guest area, plus additional unfinished storage space for future expansion. Professionally landscaped grounds feature a storage shed and maintenance-free Trex deck, perfect for outdoor entertaining.

4 Beds ⋅ 3 Baths ⋅ 24160410 MLS

HIGHEST & BEST OFFERS DUE BY NOON ON MONDAY, 4/13/26 - Fantastic opportunity to own this beautifully maintained 4-bedroom, 2.5-bath Colonial on lovely cul-de-sac neighborhood, privately set back on a wooded lot which backs up to Land Trust in sought-after Bear Run Estates. Proudly offered by its original owners, this home features numerous updates including a high-efficiency propane furnace (2023), central A/C (2024), and whole-house Generac generator (2023). A welcoming 2-story foyer leads to a fantastic eat-in kitchen with granite countertops, tiled backsplash, stainless steel appliances, breakfast bar, under-cabinet lighting, and pantry. The desirable open floor plan flows into the inviting family room with a propane fireplace and custom bookshelves. A private home office with a wall of built-ins, formal dining room, separate living room, and powder room with laundry complete the main level, all with beautiful hardwood flooring. Upstairs, the spacious primary bedroom suite offers exposed beams, walk-in closet, and renovated bath with soaking tub, tiled walk-in shower, and heated floors. Three additional generously sized bedrooms share a full bath. The walk-out lower level provides flexible finished space for a recreation room, gym, or guest area, plus additional unfinished storage space for future expansion. Professionally landscaped grounds feature a storage shed and maintenance-free Trex deck, perfect for outdoor entertaining.

54 Bear Run, Woodbury

$750,000

Beautifully Spacious Colonial in the Heart of Woodbury. This inviting in-town colonial offers the perfect balance of charm and convenience-just 5 minutes from town parks, top-rated Woodbury schools, shopping, and restaurants. Freshly refinished hardwood floors bring a warm glow throughout the home's 3,200 sq. ft. of well-crafted living space. The main level features a sun-filled kitchen and great room with 9-foot ceilings, a center island, eat-in area, and a cozy fireplace. A welcoming living and dining room, a practical mud/laundry room, and a private office with elegant French doors complete the first floor. Upstairs, you'll find three generously sized bedrooms, along with a primary suite with a walk-in closet and luxurious bath. A versatile recreation room with built-in bookshelves-accessible from both the main hall and the primary suite-offers the perfect space for a library, playroom, or studio. Set on a level lot, the home invites outdoor enjoyment with a private back deck, a charming front porch, and ample room for weekend gatherings.

4 Beds ⋅ 3 Baths ⋅ 24132227 MLS

Beautifully Spacious Colonial in the Heart of Woodbury. This inviting in-town colonial offers the perfect balance of charm and convenience-just 5 minutes from town parks, top-rated Woodbury schools, shopping, and restaurants. Freshly refinished hardwood floors bring a warm glow throughout the home's 3,200 sq. ft. of well-crafted living space. The main level features a sun-filled kitchen and great room with 9-foot ceilings, a center island, eat-in area, and a cozy fireplace. A welcoming living and dining room, a practical mud/laundry room, and a private office with elegant French doors complete the first floor. Upstairs, you'll find three generously sized bedrooms, along with a primary suite with a walk-in closet and luxurious bath. A versatile recreation room with built-in bookshelves-accessible from both the main hall and the primary suite-offers the perfect space for a library, playroom, or studio. Set on a level lot, the home invites outdoor enjoyment with a private back deck, a charming front porch, and ample room for weekend gatherings.

118 Good Hill Rd, Woodbury

$740,000

Center Hall Colonial with Full In-Law! This majestic brick facing home flaunts its location atop a private lot overlooking sprawling scenic views. Main level features a two-story foyer, formal dining room w/hardwoods & pocket doors leading to a high-end kitchen w/stainless steel appliances including a gas stove. The kitchen delivers with granite tops, upscale cabinetry, breakfast bar, & eat-in area facing French doors opening to a welcoming living room w/hardwood, vaulted ceilings & brick fireplace. The family room/study pulls in the strength of hardwoods, tray ceiling & plenty of natural lighting. The main level bedroom/office & guest bathroom complete this central level. Continuing the journey upstairs & you will be greeted by spectacular views from the transom window aloft the staircase. The path to the primary bedroom suite introduces a tray ceiling, large walk-in closet & full bath w/whirlpool tub, shower stall & skylight. The three additional bedrooms are generous in size while the laundry room, common full bath w/double sink vanity & tub/shower concludes this upper level. The main level full in-law is a desirable focal point showcasing a separate entry, remodeled eat-in kitchen, living room w/vaulted ceiling, gas fireplace, large bedroom, remodeled full bath, laundry closet & staircase to garage w/private basement. Exterior features two new A/C condenser units, custom retaining walls, large deck & three car garage. This sought-after home exceeds all expectations!

5 Beds ⋅ 4 Baths ⋅ 24171620 MLS

Center Hall Colonial with Full In-Law! This majestic brick facing home flaunts its location atop a private lot overlooking sprawling scenic views. Main level features a two-story foyer, formal dining room w/hardwoods & pocket doors leading to a high-end kitchen w/stainless steel appliances including a gas stove. The kitchen delivers with granite tops, upscale cabinetry, breakfast bar, & eat-in area facing French doors opening to a welcoming living room w/hardwood, vaulted ceilings & brick fireplace. The family room/study pulls in the strength of hardwoods, tray ceiling & plenty of natural lighting. The main level bedroom/office & guest bathroom complete this central level. Continuing the journey upstairs & you will be greeted by spectacular views from the transom window aloft the staircase. The path to the primary bedroom suite introduces a tray ceiling, large walk-in closet & full bath w/whirlpool tub, shower stall & skylight. The three additional bedrooms are generous in size while the laundry room, common full bath w/double sink vanity & tub/shower concludes this upper level. The main level full in-law is a desirable focal point showcasing a separate entry, remodeled eat-in kitchen, living room w/vaulted ceiling, gas fireplace, large bedroom, remodeled full bath, laundry closet & staircase to garage w/private basement. Exterior features two new A/C condenser units, custom retaining walls, large deck & three car garage. This sought-after home exceeds all expectations!

17 Carriage Ln, Woodbury

$732,200

The iconic Lewis Building is in a prime location at the intersection of Rt 6 and Rt 317, next to the town office buildings and library. Can't beat this location! It offers a valuable opportunity for those looking to leverage the growth and vibrancy of the area. MSD zoning offers 3 commercial rentals and 3 residential rentals. Fully occupied with little turnaround. Rents generate a great income. Well maintained with recent upgrades. With excellent visibility this investment opportunity is not to be missed.

6 Baths ⋅ 24125766 MLS

The iconic Lewis Building is in a prime location at the intersection of Rt 6 and Rt 317, next to the town office buildings and library. Can't beat this location! It offers a valuable opportunity for those looking to leverage the growth and vibrancy of the area. MSD zoning offers 3 commercial rentals and 3 residential rentals. Fully occupied with little turnaround. Rents generate a great income. Well maintained with recent upgrades. With excellent visibility this investment opportunity is not to be missed.

289 Main St S, Woodbury

$725,000

Welcome to Eastfield Farms Etates. This Colonial features an open floor plan for comfortable everyday living an entertaining alike. The large foyer flows to both the formal living room with french doors and formal dining room. Both with crown molding and accent lighting. Just down the hall step into the spacious kitchen with center island, granite counter tops stainless appliances. The dining area flows to the family room with stone wood burning fireplace and french doors leading the the back deck. The laundry room is conveniently located on the main level through the mud room. Round out the first floor with a half bath. Hardwood floors throughout the first floor. The upper level offers primary bedroom with four closets and a large bathroom with jetted tub and double sink vanity. The second bedroom is large enough to have its own seating area. There are two other bedrooms and a large bathroom. The attic has pull-down stairs. The basement is unfinished with plenty of storage. You will enjoy this lovely level landscaped spacious yard, two car attached garage and full shed. Convenielty located to Watertown and Middlebury, 90 minutes to NY City.

4 Beds ⋅ 4 Baths ⋅ 24137870 MLS

Welcome to Eastfield Farms Etates. This Colonial features an open floor plan for comfortable everyday living an entertaining alike. The large foyer flows to both the formal living room with french doors and formal dining room. Both with crown molding and accent lighting. Just down the hall step into the spacious kitchen with center island, granite counter tops stainless appliances. The dining area flows to the family room with stone wood burning fireplace and french doors leading the the back deck. The laundry room is conveniently located on the main level through the mud room. Round out the first floor with a half bath. Hardwood floors throughout the first floor. The upper level offers primary bedroom with four closets and a large bathroom with jetted tub and double sink vanity. The second bedroom is large enough to have its own seating area. There are two other bedrooms and a large bathroom. The attic has pull-down stairs. The basement is unfinished with plenty of storage. You will enjoy this lovely level landscaped spacious yard, two car attached garage and full shed. Convenielty located to Watertown and Middlebury, 90 minutes to NY City.

432 Quassapaug Rd, Woodbury

$720,000

The Woodlands

2 Beds ⋅ 3 Baths ⋅ 913014 MLS

The Woodlands

45 W Aspen, Woodbury

$715,000

Welcome to The Woodlands, a prestigious community in the heart of Woodbury. This is a rare opportunity to own the largest Cedarwood model, complete with a finished basement offering exceptional additional living space. Over 2150 square feet, this spacious condo features 3 bedrooms, 3 full bathrooms, a den, and a private two-car driveway. Sliding glass doors lead to a patio, perfect for relaxing or entertaining. Additional exterior storage adds everyday convenience. Enjoy country club living with outstanding amenities, including swimming pools, illuminated Har-Tru tennis and pickleball courts, basketball, a playground, and a clubhouse featuring a gym, card room, and party room. The community also handles snow removal, landscaping, and garbage service for easy, low-maintenance living. Ideally located near shopping, restaurants, schools, and just blocks from the Town of Oyster Bay Golf Course. Highly regarded Syosset School District (Baylis Elementary and H.B. Thompson Middle School). Don’t miss the opportunity to make this exceptional home your own.

3 Beds ⋅ 3 Baths ⋅ 960427 MLS

Welcome to The Woodlands, a prestigious community in the heart of Woodbury. This is a rare opportunity to own the largest Cedarwood model, complete with a finished basement offering exceptional additional living space. Over 2150 square feet, this spacious condo features 3 bedrooms, 3 full bathrooms, a den, and a private two-car driveway. Sliding glass doors lead to a patio, perfect for relaxing or entertaining. Additional exterior storage adds everyday convenience. Enjoy country club living with outstanding amenities, including swimming pools, illuminated Har-Tru tennis and pickleball courts, basketball, a playground, and a clubhouse featuring a gym, card room, and party room. The community also handles snow removal, landscaping, and garbage service for easy, low-maintenance living. Ideally located near shopping, restaurants, schools, and just blocks from the Town of Oyster Bay Golf Course. Highly regarded Syosset School District (Baylis Elementary and H.B. Thompson Middle School). Don’t miss the opportunity to make this exceptional home your own.

61 Estate Court Unit #61, Woodbury

$712,000

Enjoy a country club lifestyle in the desirable Woodbury Village Community with Syosset Schools! Summer fun can be found in the outdoor pool, tennis, pickleball courts & playground! Move-In Ready, this spacious 2–3 bedroom, 2.5 bath townhouse features an eat in granite kitchen with stainless steel appliances & abundant cabinetry, kitchen bay window, vaulted ceilings & skylights. The open-concept sun-drenched L-shaped living/dining room has crown molding, wood-burning fireplace and sliders that open onto the lovely brick patio for outdoor entertaining. The primary suite includes a private bath & two oversized closets. A large second bedroom has a private hall bath. The open loft/office can easily be converted into a third bedroom. Additional storage is available in the pull-down attic. Ample closets, guest half bath on first floor & laundry in the unit complete this perfect home. Conveniently located near shopping, dining, LIRR, and hiking trails!

3 Beds ⋅ 3 Baths ⋅ 1004934 MLS

Enjoy a country club lifestyle in the desirable Woodbury Village Community with Syosset Schools! Summer fun can be found in the outdoor pool, tennis, pickleball courts & playground! Move-In Ready, this spacious 2–3 bedroom, 2.5 bath townhouse features an eat in granite kitchen with stainless steel appliances & abundant cabinetry, kitchen bay window, vaulted ceilings & skylights. The open-concept sun-drenched L-shaped living/dining room has crown molding, wood-burning fireplace and sliders that open onto the lovely brick patio for outdoor entertaining. The primary suite includes a private bath & two oversized closets. A large second bedroom has a private hall bath. The open loft/office can easily be converted into a third bedroom. Additional storage is available in the pull-down attic. Ample closets, guest half bath on first floor & laundry in the unit complete this perfect home. Conveniently located near shopping, dining, LIRR, and hiking trails!

12 Hampton Way, Woodbury

$710,000

Located in picturesque Woodbury, voted Most Charming Town in CT by Reader's Digest in 2018, 2020 and 2024 and featured by Travel + Leisure among the 10 Best Places to Live. This stately circa 1845 home blends historic character with comfortable living. Set along scenic Good Hill Road and surrounded by lush, established gardens, featuring a black bottom gunite pool, private terrace, welcoming front porch, and charming potting shed, creating a peaceful retreat. Inside, a sun-filled front-to-back living room offers elegant moldings, custom built-ins, and a wood-burning fireplace. The adjacent study, with built-in bookcases and a second wood-burning fireplace, provides an ideal home office or quiet sitting room. The warm and functional kitchen includes solid wood, custom cabinetry, a brand-new Thor stove, and a breakfast nook. A versatile side room, with full bath, offers flexibility for a pantry, office, or first-floor bedroom. The dining room, just beyond the wet bar, overlooks the terrace and is perfect for gatherings. Upstairs are three spacious bedrooms and two full baths, including a primary bedroom with fireplace, wall of closets and private en-suite. Cedar-lined closets are found throughout. A classic two-story barn provides three-car parking plus ample storage or hobby space and an area to lounge by the pool. Central air and a whole-house generator complete this idyllic country retreat. Good Hill leads directly to Main St. and Hollow Park, road construction ends in May

3 Beds ⋅ 4 Baths ⋅ 24155513 MLS

Located in picturesque Woodbury, voted Most Charming Town in CT by Reader's Digest in 2018, 2020 and 2024 and featured by Travel + Leisure among the 10 Best Places to Live. This stately circa 1845 home blends historic character with comfortable living. Set along scenic Good Hill Road and surrounded by lush, established gardens, featuring a black bottom gunite pool, private terrace, welcoming front porch, and charming potting shed, creating a peaceful retreat. Inside, a sun-filled front-to-back living room offers elegant moldings, custom built-ins, and a wood-burning fireplace. The adjacent study, with built-in bookcases and a second wood-burning fireplace, provides an ideal home office or quiet sitting room. The warm and functional kitchen includes solid wood, custom cabinetry, a brand-new Thor stove, and a breakfast nook. A versatile side room, with full bath, offers flexibility for a pantry, office, or first-floor bedroom. The dining room, just beyond the wet bar, overlooks the terrace and is perfect for gatherings. Upstairs are three spacious bedrooms and two full baths, including a primary bedroom with fireplace, wall of closets and private en-suite. Cedar-lined closets are found throughout. A classic two-story barn provides three-car parking plus ample storage or hobby space and an area to lounge by the pool. Central air and a whole-house generator complete this idyllic country retreat. Good Hill leads directly to Main St. and Hollow Park, road construction ends in May

58 Good Hill Rd, Woodbury

$707,000

Nestled within the exclusive South Brook community, 19 Hill View Lane offers timeless New England charm paired with exceptional craftsmanship. This beautifully appointed 3 bedroom, 3.5 bath cape colonial is rich in architectural detail, featuring refined millwork, quality finishes, and a thoughtful layout designed for both everyday living and elegant entertaining. The main living spaces flow effortlessly, filled with natural light and a warm, inviting ambiance that immediately feels like home. Beneath the main living area lies a space designed purely for enjoyment. The finished lower level features a Roman-style sauna, wet bar, recreation room, and a full bath, creating the perfect space for entertaining, relaxing, or unwinding at the end of the day. Set on a picturesque lot within a quiet, well maintained neighborhood, this home offers a rare blend of privacy and community. Residents enjoy award-winning dining, entertainment and boutique shopping within just a quarter mile from home. Located just minutes from the historic town center of Woodbury, scenic parks and highly regarded schools all while being centrally positioned for easy access throughout Litchfield County. A truly special home where classic design meets refined living. Association rules apply.

3 Beds ⋅ 4 Baths ⋅ 24147161 MLS

Nestled within the exclusive South Brook community, 19 Hill View Lane offers timeless New England charm paired with exceptional craftsmanship. This beautifully appointed 3 bedroom, 3.5 bath cape colonial is rich in architectural detail, featuring refined millwork, quality finishes, and a thoughtful layout designed for both everyday living and elegant entertaining. The main living spaces flow effortlessly, filled with natural light and a warm, inviting ambiance that immediately feels like home. Beneath the main living area lies a space designed purely for enjoyment. The finished lower level features a Roman-style sauna, wet bar, recreation room, and a full bath, creating the perfect space for entertaining, relaxing, or unwinding at the end of the day. Set on a picturesque lot within a quiet, well maintained neighborhood, this home offers a rare blend of privacy and community. Residents enjoy award-winning dining, entertainment and boutique shopping within just a quarter mile from home. Located just minutes from the historic town center of Woodbury, scenic parks and highly regarded schools all while being centrally positioned for easy access throughout Litchfield County. A truly special home where classic design meets refined living. Association rules apply.

19 Hillview Ln, Woodbury

$705,000

Experience the ease of single-level living in this lovingly maintained residence. Nestled on a private lot bordering acres of open space, this home is a study in thoughtful design and architectural detail. The interior is defined by a sense of scale and light, featuring hardwood floors, elegant tray ceilings, and custom crown moldings. At the heart of the home, the spacious living room is anchored by a classic fireplace and handsome built-ins. The eat-in kitchen invites warmth with the "chestnut glow" of its cabinetry, beautifully paired with polished granite countertops and a convenient breakfast bar. Seamlessly blending indoor and outdoor living, the home features a three-season sunroom, complete with a "family room" style fireplace-the perfect setting for crisp New England evenings. Designed for ultimate privacy, the "split-wing" floor plan separates the guest quarters-where the bedrooms share a refined marble-clad bath-from the expansive primary suite. This sanctuary features a walk-in closet and a versatile in-room nook, perfect for a private seating area or workspace. For the professional, a dedicated separate office rounds out the living areas.

3 Beds ⋅ 3 Baths ⋅ 24152365 MLS

Experience the ease of single-level living in this lovingly maintained residence. Nestled on a private lot bordering acres of open space, this home is a study in thoughtful design and architectural detail. The interior is defined by a sense of scale and light, featuring hardwood floors, elegant tray ceilings, and custom crown moldings. At the heart of the home, the spacious living room is anchored by a classic fireplace and handsome built-ins. The eat-in kitchen invites warmth with the "chestnut glow" of its cabinetry, beautifully paired with polished granite countertops and a convenient breakfast bar. Seamlessly blending indoor and outdoor living, the home features a three-season sunroom, complete with a "family room" style fireplace-the perfect setting for crisp New England evenings. Designed for ultimate privacy, the "split-wing" floor plan separates the guest quarters-where the bedrooms share a refined marble-clad bath-from the expansive primary suite. This sanctuary features a walk-in closet and a versatile in-room nook, perfect for a private seating area or workspace. For the professional, a dedicated separate office rounds out the living areas.

43 Mill Rd, Woodbury

$700,000

Watch the parade from your front yard, walk to school, walk to the excellent restaurants in town, walk to the library and to the local park and market! Fabulous location! One of Woodbury's last remaining homes built in the late 1600s. This charming residence offers a unique blend of historic character and modern convenience, ideally situated for those who appreciate easy access to local shops, parks, and restaurants. The interior of the home boasts a rich history with exposed wooden beams, 4 fireplaces, and classic hardwood floors, creating an inviting and warm atmosphere. Outside, a private patio with an open fireplace provides an ideal setting for relaxation or entertaining, surrounded by lush perennial gardens. Adding to the property's versatility is a separate guest house. This additional structure is perfect for an artist's studio, offering a quiet and inspiring space for creative pursuits, or it can serve as a professional office. Woodbury is known for its historical properties, with some homes dating back to the late 17th century. Main Street offers a charming experience with its antique shops, local restaurants, and vibrant Memorial Day parades. Woodbury is known for its picturesque downtown area, featuring beautiful streets and historic houses. Litchfield Hills are home to numerous wineries, forming part of Connecticut's Wine Trail,where you can enjoy tastings and scenic vineyards. The region also boasts farm-to-table restaurants that highlight local produce

4 Beds ⋅ 3 Baths ⋅ 24165323 MLS

Watch the parade from your front yard, walk to school, walk to the excellent restaurants in town, walk to the library and to the local park and market! Fabulous location! One of Woodbury's last remaining homes built in the late 1600s. This charming residence offers a unique blend of historic character and modern convenience, ideally situated for those who appreciate easy access to local shops, parks, and restaurants. The interior of the home boasts a rich history with exposed wooden beams, 4 fireplaces, and classic hardwood floors, creating an inviting and warm atmosphere. Outside, a private patio with an open fireplace provides an ideal setting for relaxation or entertaining, surrounded by lush perennial gardens. Adding to the property's versatility is a separate guest house. This additional structure is perfect for an artist's studio, offering a quiet and inspiring space for creative pursuits, or it can serve as a professional office. Woodbury is known for its historical properties, with some homes dating back to the late 17th century. Main Street offers a charming experience with its antique shops, local restaurants, and vibrant Memorial Day parades. Woodbury is known for its picturesque downtown area, featuring beautiful streets and historic houses. Litchfield Hills are home to numerous wineries, forming part of Connecticut's Wine Trail,where you can enjoy tastings and scenic vineyards. The region also boasts farm-to-table restaurants that highlight local produce

339 Main St S, Woodbury

$699,000

Meticulously maintained and handsomely set on a picturesque lot in charming Woodbury, Connecticut, this classic Colonial offers the perfect blend of timeless character, comfort, and outdoor beauty. From the moment you arrive, the home makes a lasting impression with its mature tree-lined setting, stone walls, flowering gardens, cobblestone and bluestone walkway, and inviting front entry. Inside, sun-drenched rooms create a warm and welcoming atmosphere, giving the home an immediate sense of comfort and ease. Thoughtful details, generous living spaces, and a graceful floor plan make this a home that feels both elegant and truly livable. The inviting living and dining areas flow beautifully for everyday living and entertaining, while the bedrooms offer peaceful retreats filled with natural light. The primary suite is a special highlight, featuring its own Romeo and Juliet balcony overlooking the gardens and professionally maintained grounds. It is the kind of private, charming detail that gives the home a rare sense of romance and character. Outdoor living is just as impressive. Enjoy a private bluestone patio, beautifully framed by stonework and landscaping, along with a spacious Trex back deck designed for relaxing, dining, and entertaining. Whether enjoying morning coffee, summer gatherings, or quiet evenings surrounded by nature, the property offers a peaceful country setting while still being close to the charm, shops, restaurants, and conveniences of Woodbury.

3 Beds ⋅ 3 Baths ⋅ 24185444 MLS

Meticulously maintained and handsomely set on a picturesque lot in charming Woodbury, Connecticut, this classic Colonial offers the perfect blend of timeless character, comfort, and outdoor beauty. From the moment you arrive, the home makes a lasting impression with its mature tree-lined setting, stone walls, flowering gardens, cobblestone and bluestone walkway, and inviting front entry. Inside, sun-drenched rooms create a warm and welcoming atmosphere, giving the home an immediate sense of comfort and ease. Thoughtful details, generous living spaces, and a graceful floor plan make this a home that feels both elegant and truly livable. The inviting living and dining areas flow beautifully for everyday living and entertaining, while the bedrooms offer peaceful retreats filled with natural light. The primary suite is a special highlight, featuring its own Romeo and Juliet balcony overlooking the gardens and professionally maintained grounds. It is the kind of private, charming detail that gives the home a rare sense of romance and character. Outdoor living is just as impressive. Enjoy a private bluestone patio, beautifully framed by stonework and landscaping, along with a spacious Trex back deck designed for relaxing, dining, and entertaining. Whether enjoying morning coffee, summer gatherings, or quiet evenings surrounded by nature, the property offers a peaceful country setting while still being close to the charm, shops, restaurants, and conveniences of Woodbury.

674 Middle Road Tpke, Woodbury

$695,000

Turn-key elevated ranch with in-ground pool, and immaculate grounds. Set on 1.6+ park-like acres, this modern ranch includes 3 bed/3 full baths, a 3-season screened porch, and a heated 20x40 pool with an oversized concrete patio. The living areas and recently renovated eat-in chef's kitchen shine with custom island, top-of-the-line appliances, and a dedicated butler's pantry with sink, wine fridge, and shelving. From the kitchen, enter the dedicated dining room with custom built-ins which open to the vaulted great room with floor-to-ceiling stone fireplace and locally sourced reclaimed mantle. Doors open out to a new composite deck overlooking the private, professionally landscaped grounds with overflowing hydrangeas, Japanese maples, and fruit trees. The primary suite features a custom cedar walk-in closet and en-suite bath. Two additional bedrooms and updated full bath provide comfortable living for family and guests. A secondary sunlit living room with an efficient pellet stove adds cozy warmth which opens out to a 3-season porch. The finished lower level includes a full bath and versatile space - perfect for a gym, media room, or flex space. Outside, enjoy true resort-style living around the fully fenced pool complex. Additional exterior highlights include a horseshoe pea gravel driveway, 4 y.o. architectural roof, new pool pump/filter and two storage sheds. Located just minutes to Woodbury's historic town center, fine dining, and boutique shopping!

3 Beds ⋅ 3 Baths ⋅ 24197319 MLS

Turn-key elevated ranch with in-ground pool, and immaculate grounds. Set on 1.6+ park-like acres, this modern ranch includes 3 bed/3 full baths, a 3-season screened porch, and a heated 20x40 pool with an oversized concrete patio. The living areas and recently renovated eat-in chef's kitchen shine with custom island, top-of-the-line appliances, and a dedicated butler's pantry with sink, wine fridge, and shelving. From the kitchen, enter the dedicated dining room with custom built-ins which open to the vaulted great room with floor-to-ceiling stone fireplace and locally sourced reclaimed mantle. Doors open out to a new composite deck overlooking the private, professionally landscaped grounds with overflowing hydrangeas, Japanese maples, and fruit trees. The primary suite features a custom cedar walk-in closet and en-suite bath. Two additional bedrooms and updated full bath provide comfortable living for family and guests. A secondary sunlit living room with an efficient pellet stove adds cozy warmth which opens out to a 3-season porch. The finished lower level includes a full bath and versatile space - perfect for a gym, media room, or flex space. Outside, enjoy true resort-style living around the fully fenced pool complex. Additional exterior highlights include a horseshoe pea gravel driveway, 4 y.o. architectural roof, new pool pump/filter and two storage sheds. Located just minutes to Woodbury's historic town center, fine dining, and boutique shopping!

39 Hard Hill Rd, Woodbury

$680,000

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

3 Beds ⋅ 3 Baths ⋅ 24190540 MLS

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

31 Mountain Rd, Woodbury

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