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46 Grassy Hill Rd, Woodbury
$1,275,000
4 Beds ⋅ 4 Baths ⋅ 24188752 MLS
Beautifully updated and impeccably maintained, this custom Colonial offers timeless New England charm in a private setting with gorgeous views of a picturesque waterfall and babbling brook. Set on beautifully landscaped grounds with an additional lot included, the home features wide-board hardwood floors, crown molding, custom built-ins, plantation shutters, French doors, and three fireplaces. The eat-in kitchen offers granite countertops, premium appliances, and opens to warm, inviting living spaces including formal living and dining rooms, a family room with fireplace, private den/office, and screened porch. The spacious primary suite includes a fireplace, walk-in closet, and ensuite bath, with three additional bedrooms and updated bathrooms. The finished walk-out lower level provides flexible space for a recreation room, gym, media room, or guests. Outdoor living is exceptional with a wraparound porch, Trex deck, extensive stone patios, mature landscaping, scenic trails, and the soothing sights and sounds of the cascading waterfall. A rare offering combining privacy, elegance, upgrades, and natural beauty just minutes from town.

46 Grassy Hill Rd, Woodbury

419 Woodbury Road, Woodbury
$1,250,000
4 Beds ⋅ 4 Baths ⋅ 872208 MLS
Welcome to this spacious and sun-filled 4-bedroom, 3.5-bath home set on 1.75 acres of flat, park-like property in the heart of Woodbury, within the top-rated Syosset School District. The home's generous layout is designed for both comfort and possibility, featuring a warm and inviting living room with a classic wood-burning fireplace and a den surrounded by windows that frame peaceful backyard views. It also includes a walkout basement, offering flexible space for recreation, a home office, or multigenerational living. While some updates may be desired to align with your personal style, the home is move-in ready—allowing you to enjoy it now while planning your dream design at your own pace. Step outside to a large covered porch—perfect for relaxing, entertaining, or simply enjoying the serenity of your private landscape. Whether you're seeking a tranquil retreat, a place to grow, or a canvas to create your ideal living environment, this property offers rare value in a prestigious location. Come experience the space, setting, and spirit of possibility that only a property like this can provide.

419 Woodbury Road, Woodbury

68 Whittlesey Rd, Woodbury
$1,225,000
4 Beds ⋅ 4 Baths ⋅ 24130861 MLS
This magnificent Woodbury colonial, adjacent to 42 acres of open space, offers an unparalleled blend of elegance and tranquility. Surrounded by hiking trails, park like grounds and a serene brook. A light filled interior with soaring nine foot ceilings, graceful arches and an open flowing floor plan. The wraparound mahogany deck invites you to relax and take in the peace and quiet. The back patio, crafted with premium ipe decking, features tiered rock walls and a circular fire pit-perfect for entertaining or quiet evenings under the stars. Designed with quality and comfort in mind this home boasts I-beam construction, two wells, enhanced insulation, and durable HardiePlank siding, ideal for those who value sustainable, low maintenance living. Turn off the outside noise and rest assure this sanctuary will welcome you home with open arms.

68 Whittlesey Rd, Woodbury

86 Chestnut Lane, Woodbury
$1,225,000
3 Beds ⋅ 3 Baths ⋅ 910082 MLS
Located in the Woodbury Greens community, this Aspen model townhome offers three bedrooms, two full bathrooms, and one half bathroom. The main level features an open floor plan with marble flooring, a spacious living area with sliding glass doors leading to a private deck, a formal dining area, and a beautifully designed kitchen with custom cabinetry and granite countertops. Upstairs, the primary en-suite includes custom closets and a private bath, while two additional bedrooms and a full bathroom provide space for family, guests, or a home office. The finished full basement adds additional living or recreation space, and the home also includes an attached garage, in-home laundry, and well-maintained interiors. New roof and CAC. Community amenities include a pickle-ball court, tennis courts, and a pool. Conveniently located near the Town of Oyster Bay Golf Course, shopping, dining, and major roadways, all within Syosset School District. This home offers comfort, functionality, and a great location.

86 Chestnut Lane, Woodbury

863 Woodbury Road, Woodbury
$1,200,000
6 Beds ⋅ 3 Baths ⋅ 941929 MLS
Welcome to this Victorian Colonial, perfectly set on just over a half acre of property. The entry door with beautiful stained glass sets the stage for this unique home. Timeless character and charm showcase this home with 6 bedrooms, 3 full baths, two staircases, natural gas, hardwood floors, high ceilings, striking architectural details and sun-drenched rooms that create a bright and inviting space. The main level features generous sized rooms, including a formal living room and formal dining room that are ideal for both everyday living and entertaining. The updated eat-in kitchen offers modern convenience while maintaining the home’s traditional character. A spacious duplex-style guest suite on the first floor, complete with its own entrance, renovated kitchen, living room, bedroom and bath , provides exceptional living flexibility. Upstairs the second level is dedicated to five private, light-filled bedrooms with oversized windows and a full hall renovated bathroom with a clean classic style. A walk-up third floor of over 1000 square feet adds an oversized bonus space that awaits your imagination. The full basement further enhances the home’s versatility with ample storage, laundry area, mechanicals and full walk out. Outside, the expansive half acre property features an extra-large driveway and a generous yard with plenty of room to add a pool or create your ideal outdoor retreat. This elegant residence presents a rare opportunity to own a home that seamlessly blends historic charm with modern comfort. Conveniently located near shops, restaurants, parks, schools, transportation and in the highly regarded Syosset School District. (Entrance on Glenn Drive)

863 Woodbury Road, Woodbury

101 Old Grassy Hill Rd, Woodbury
$1,200,000
4 Beds ⋅ 5 Baths ⋅ 24135665 MLS
"Where Luxury Meets the Landscape." Welcome to a home where nature and craftsmanship converge in breathtaking harmony. Nestled on five professionally landscaped acres, this country manor is a sanctuary of serenity and sophistication. A statuesque quarry of stone lines one side of the property, perfectly balanced by a tranquil body of water-inviting you to kayak, canoe, or skate through the seasons or perhaps just enjoy the resident eagles or osprey who make the area their home during some of the year. As you enter, the grand open staircase is the centerpiece of a 2-story wrap-around Foyer that sets the stage for the comfortable elegance this home inspires. Step inside and experience the artistry of design. Sunlight pours through expansive windows, illuminating exquisite millwork: coffered ceilings, oversized crown and baseboard moldings, solid raised paneling, and wide-board hardwood floors. Every detail speaks to the builder's commitment to timeless quality. The grounds are thoughtfully engineered for beauty and function-featuring a level yard with industrial grade drainage, a low-maintenance milled crushed stone driveway, double-tiered decking, and a refreshing outdoor shower along with new stone seating area, walkways in the backyard.

101 Old Grassy Hill Rd, Woodbury

6 Wren Drive, Woodbury
$1,190,000
3 Beds ⋅ 4 Baths ⋅ 974203 MLS
Welcome to this spacious split-level home located in the highly sought-after Syosset School District. Offering generous living spaces throughout, this home features 3 bedrooms and 3.5 bathrooms, including a primary bedroom ensuite for added comfort and privacy. The oversized dining room is perfect for entertaining, while the inviting living areas showcase beautiful hardwood floors, two fireplaces and abundant natural light enhanced by skylights. The updated kitchen is equipped with stainless steel appliances, granite countertops, natural gas cooking and convenient access to an outdoor deck—ideal for everyday living and gatherings. Additional highlights include a whole-house generator, a new Navien boiler, Andersen windows and new vinyl siding for peace of mind. The home also offers a 2-car garage, a basement with an additional bathroom and sliders leading to a paved patio for outdoor enjoyment. Perfectly situated near highways, schools, shopping and restaurants, this home combines comfort, functionality, and an unbeatable location.

6 Wren Drive, Woodbury

203 Woodbury Road, Woodbury
$1,120,000
5 Beds ⋅ 3 Baths ⋅ 966319 MLS
Welcome home to 203 Woodbury Road! This expansive 5-bedroom, 3-full-bathroom Hi-Ranch offers over 2,600 square feet of versatile living space. Built in 1988, this incredible property has been lovingly maintained by its original owners and pride of ownership truly shines throughout. A standout feature of this home is the highly desirable main-level layout. It boasts a spacious first-floor bedroom complete with a separate entrance and a full bathroom—making it the perfect setup for extended family, guests, or a private home office. The main level also features a welcoming family room, an additional bedroom (currently set up as a home gym!), and convenient access to the attached 2-car garage. Upstairs, the bright and airy main floor features a spacious living room, a formal dining room, and a kitchen ready for your personal touch. This level also hosts the primary bedroom alongside two additional bedrooms and two full baths. A unique find for this home is the unfinished basement! This incredible bonus area provides an abundance of extra storage space or a blank canvas for your future needs. Additional features: Updated kitchen, baths, roof, gutters and more. Don't miss this rare opportunity to make this cherished house your new home!

203 Woodbury Road, Woodbury

26 Jennings Lane, Woodbury
$1,100,000
3 Beds ⋅ 3 Baths ⋅ 1028929 MLS
The largest model in the highly sought-after Woodlands community, this beautifully renovated end-unit residence offers approximately 2,355 square feet of well-designed living space with an open floor plan, soaring two-story ceilings, and the privacy and abundant natural light of a desirable end-unit location. The spacious living and dining rooms flow effortlessly together and open through sliding glass doors to a private Trex deck, extending the living space outdoors to the backyard. A versatile den features a large walk-in storage closet plus an additional windowed alcove, ideal for a workspace or extra storage. The renovated kitchen opens to the main living areas, while the expanded primary suite includes a beautifully enlarged bath with a soaking tub, separate shower, and exceptional storage, a rare enhancement unique to this model. The oversized finished lower level offers exceptional flexibility with expansive recreation space, abundant storage, and a separate room ideal for a home office, gym, media room, or overnight guests. Ideally located in the heart of Woodbury, The Woodlands offers a convenient lifestyle just minutes from shopping, restaurants, parks, golf courses, the Long Island Rail Road, and major parkways, all within the award-winning Syosset Central School District. Residents also enjoy exceptional community amenities including a clubhouse with a fitness center, party room, card room, swimming pool, tennis and pickleball courts, basketball court, and playground.

26 Jennings Lane, Woodbury

61 Silver Brook Ln, Woodbury
$1,069,900
4 Beds ⋅ 4 Baths ⋅ 24177448 MLS
Exceptional Colonial in one of Woodbury's finest developments, beautifully set among similar distinguished homes at the end of Silver Brook Lane. Thoughtfully updated over the past five years with high-quality materials and careful attention to detail, this 4,000+ square foot residence offers an ideal blend of elegance, comfort, and modern convenience. The heart of the home is the stunning remodeled eat-in kitchen, complete with a large center island and all the features expected in a gourmet kitchen. The kitchen opens seamlessly to a generous family room with fireplace, coffered ceiling, and access to the rear level deck, creating a wonderful flow for everyday living and entertaining. The main level also includes a private office, formal living room, and formal dining room, all enhanced by hardwood floors and moldings. Upstairs, the luxurious primary suite features a dressing room or office, two walk-in closets, a soaking tub, and a custom tiled shower. Three additional bedrooms complete the upper level, including two with en-suite baths and one with an open stairway leading to a third floor sleeping area.

61 Silver Brook Ln, Woodbury

54 Estate Court Unit #54, Woodbury
$1,040,000
4 Beds ⋅ 3 Baths ⋅ 965549 MLS
Magnificent, spacious and beautifully updated, this rare 4 Bedroom | 3 Full Bath Woodlands Condo offers comfortable, move-in ready living in one of Woodbury’s most sought-after communities. The home features a luxurious open floor plan highlighted by a renovated eat-in kitchen with quartzite countertops, designer tile backsplash, updated flooring, and LED lighting throughout. A first-floor full bath with shower adds convenience and flexibility for guests or extended living. The sun-filled dining area flows seamlessly to a private outdoor setting, creating the perfect space for relaxing or entertaining. The generously sized primary suite offers a thoughtful layout, privacy, and ample storage. Updates completed within the most recent 3–4 years include refreshed vanities, modern appliances, mechanical improvements including boiler and tank, and continued interior enhancements that reflect pride of ownership. Residents enjoy The Woodlands lifestyle with resort-style amenities including tennis, pickleball, pool, clubhouse with racquetball, gym, playground, and beautifully maintained grounds. Spacious, updated, and ideally located — this exceptional home offers low-maintenance living with the feel of a private residence. Appearance: Diamond

54 Estate Court Unit #54, Woodbury

52 Holiday Drive Unit #52, Woodbury
$999,000
3 Beds ⋅ 3 Baths ⋅ 995603 MLS
ALL UPDATED - CEDARWOOD MODEL IN WOODLAND POND - SYOSSET SCHOOLS. Welcome to your next chapter in the highly sought-after Woodland Pond community—with community pool, tennis, clubhouse & more. This beautifully updated townhome has it all, featuring a private 2-car driveway and spacious 2-car garage. Inside, you’ll immediately notice the rich, new floors that flow seamlessly across the main level, paired with thoughtfully chosen modern finishes completed within the last 1–3 years—so you can simply unpack and start living. Imagine preparing meals in your fully updated eat-in kitchen, equipped with new stainless steel appliances, sleek Quartz countertops, and updated fixtures that make everyday living feel elevated. The open layout and hi-hat lighting throughout create a bright, inviting atmosphere. Upstairs, retreat to your spacious primary suite—a calming sanctuary with a full bath and generous closet space and extra storage. Two additional bedrooms, a full bath, and a sunlit loft with skylight offer flexibility for guests, a home office, a cozy reading nook, or even an upstairs playroom. Step outside through sliding glass doors to your private Trex deck, framed by lush privacy plantings—an ideal setting for entertaining or simply unwinding at the end of the day. Every detail has been thoughtfully upgraded for peace of mind and modern convenience, including new flooring, updated baths, washer/dryer, alarm system, upgraded heating system, and a new boiler. As part of Woodland Pond, you’ll enjoy resort-style amenities—tennis courts, basketball court, heated outdoor pool, and a newly renovated clubhouse with fitness center, card rooms, and event spaces—enhancing your lifestyle year-round. Located within the acclaimed Syosset School District, this home offers not just a place to live, but a lifestyle to love. Homes like this—fully updated, move-in ready, and perfectly positioned—don’t come along often. Experience it for yourself before it’s gone. (More pix coming soon)

52 Holiday Drive Unit #52, Woodbury

141 Woodlake Drive E, Woodbury
$990,000
3 Beds ⋅ 3 Baths ⋅ 897121 MLS
Located in the desirable Woodland Pond community, this fully renovated 3-bedroom, 2.5-bath townhouse offers the perfect blend of modern design, comfort, and convenience. Inside, you'll find gleaming hardwood floors, elegant wainscoting, and a bright, open layout. Sliding glass doors lead to a Trex deck, perfect for relaxing or entertaining outdoors. Upstairs, the hallway features soaring ceilings and a skylight, flooding the space with natural light. The spacious primary suite includes a beautifully updated ensuite bath, while two additional bedrooms share another stylish, brand-new bathroom. A large finished basement expands your living space, complete with a media area, playroom, and plenty of flexible space for a home office, gym, or guests—whatever suits your lifestyle. Enjoy resort-style amenities including tennis and pickleball courts, basketball, a gym, clubhouse with card and party rooms, in-ground pool, kiddie pool, and a playground. Just minutes to shopping, dining, highways, and the train—and part of the top-rated Syosset School District—this home truly has it all.

141 Woodlake Drive E, Woodbury

25 Curtiss Mdws, Woodbury
$970,000
4 Beds ⋅ 4 Baths ⋅ 24107125 MLS
Live your best life in Woodbury, CT, where charm, history, and natural beauty intertwine! The "Antiques Capital of CT", with a picturesque Main Street, historic homes, festivals, and scenic preserves. Imagine living in the heart of this idyllic setting! This 2005 home, on 4.5 acres, is meant for life, living, and entertaining. Upstairs, you'll find 4 generously sized bedrooms and 3 well-appointed bathrooms; 2 of which are ensuite, along with a convenient laundry area. On the main floor, there are living, dining, and family rooms, a half-bath, study, a dinette, and kitchen. There is a large attic and a bright walkout full basement which is partially finished with all walls and future rooms fully framed. Step outside and be amazed by the 40' in-ground heated pool, a spectacular custom-built pavilion and pool house with living-space, loft, a half bath, and a glorious outdoor shower. The star of the show is the full outdoor Viking kitchen & bar. Providing unforgettable experiences for gatherings of any size; Simple dinners or awesome larger celebrations! The expansive grounds offer the perfect mix of level terrain and picturesque hills, for outdoor fun in every season. Swimming, ATV, ball games, sledding and much more! 25 Curtiss Meadows is a camp-like getaway for close ones and friends and an immensely profound and treasured home for its residents. This gem is an absolute must-see. Don't miss the opportunity, schedule your private showing today and begin your next chapter

25 Curtiss Mdws, Woodbury

84 Aspen Drive W, Woodbury
$967,000
4 Beds ⋅ 3 Baths ⋅ 954567 MLS
Welcome to this beautifully updated 4-bedroom, 2.5-bath condo in the highly desirable Woodlands community. This home offers more than 2,000 square feet of living space and wood floors throughout. The kitchen offers plenty of cabinet space and opens to the dining area, which features sliders that lead to a private deck—ideal for entertaining or simply enjoying some fresh air. A skylight brings in natural light, adding to the airy feel of the home. Major updates include a new HVAC system and condenser, washer and dryer, and hot water heater. The home is also equipped with a first-floor laundry room and an alarm system connected to a central station. Parking is easy with a 2-car driveway and a 1-car garage. The Woodlands is a pet-friendly community with an HOA that covers snow removal, landscaping, and pool maintenance. Residents also enjoy access to tennis and pickleball courts, making it easy to stay active and connected. Some photos are virtually staged.

84 Aspen Drive W, Woodbury

137 Woodlake Drive W, Woodbury
$938,000
3 Beds ⋅ 3 Baths ⋅ 957499 MLS
Set in the desirable Woodland Pond community in Woodbury, this well-maintained, move-in ready 3-bedroom, 2.5-bath townhouse offers easy living within the top-rated Syosset School District. The home features a bright, open floor plan with sliding glass doors that fill the main level with natural light. A private driveway, attached garage, and full basement—features not found in every unit—add exceptional convenience and value. Upstairs includes a primary en-suite, two additional well-sized bedrooms, and a full hallway bath. The basement provides flexible recreational space, ideal for a playroom, home office, or gym. Enjoy resort-style amenities including tennis, pickleball, and basketball courts, a fitness center, clubhouse with party and card rooms, in-ground pool, kiddie pool, and playground. Conveniently located minutes from shopping, dining, major highways, and the train.

137 Woodlake Drive W, Woodbury

35 Coach Light Dr, Woodbury
$925,000
4 Beds ⋅ 6 Baths ⋅ 24158582 MLS
This exceptional residence welcomes you with a dramatic two-story entry and is designed for both refined entertaining and comfortable everyday living, just minutes from town. There is a formal living and dining room with rich hardwood flooring, creating a sophisticated setting for gatherings. The heart of the home is a beautifully appointed chef's kitchen featuring granite countertops, a breakfast bar, and KitchenAid and Thermador appliances. The sun-filled breakfast nook flows effortlessly into the inviting family room, where a striking stone fireplace and expansive bay window frame picturesque views of the property. A set of sliders open to a large composite deck for summer enjoyment. The second floor is highlighted by an extraordinary primary suite designed as a private retreat. This luxurious space features a spa-inspired bath, two walk-in closets, and an elegant sitting room with fireplace and built-ins, along with a private office or dressing room. Three additional en-suite bedrooms-including one currently used as a gym-offer comfort and privacy for family and guests. The partially finished walk-out lower level is filled with natural light, offering impressive 9+ foot ceilings and exceptional versatility. Anchored by a beautiful stone fireplace, the space includes two additional finished rooms and a full bath-ideal for recreation, guest accommodations, or extended living. There is a relaxing patio, peach trees, pear trees and raspberries. A must see!

35 Coach Light Dr, Woodbury

16 Sheffield Hill, Woodbury
$925,000
3 Beds ⋅ 3 Baths ⋅ 926974 MLS
Discover the best of luxury and convenience in the prestigious Woodbury Village Community, located in the top-rated Syosset School District. Enjoy a country club lifestyle with resort-style amenities including an outdoor pool, tennis and pickleball courts, and a playground — all in one of the area’s most desirable neighborhoods. This move-in-ready 3-bedroom, 2.5-bath townhouse offers an open, sun-filled layout perfect for modern living. The updated granite eat-in kitchen features stainless steel appliances and plenty of cabinet space. A spacious L-shaped living and dining room with vaulted ceilings, skylights, and a cozy wood-burning fireplace opens through sliding doors to a trex deck patio, ideal for outdoor entertaining. The primary suite includes a private bath and walk-in closet, while the additional bedrooms are bright and generously sized, sharing a well-appointed hall bath. Additional highlights include ample storage, a convenient first-floor powder room, and in-unit laundry. Ideally located near shopping, dining, the LIRR, and beautiful hiking trails, this home offers the perfect blend of style, space, and suburban ease in one of Woodbury’s most sought-after communities.

16 Sheffield Hill, Woodbury

52 Steeple View Ln, Woodbury
$922,000
4 Beds ⋅ 3 Baths ⋅ 24145387 MLS
Nestled within an established enclave of Woodbury-a quintessential New England town-this 2001 four-bedroom Colonial offers a refined blend of understated, classic architecture, and modern comfort. Ideally located just five minutes from Main Street, the home is privately sited at the end of a quiet cul-de-sac, bordered by tranquil woodlands. The interior showcases richly layered trim details, including deep crown moldings, wainscoting, and substantial baseboards in the formal spaces, creating an elegant and tailored aesthetic. The home thoughtfully balances formal entertaining areas with an open-concept layout. The gracious foyer, flanked by a formal Dining Room and a Living Room featuring custom woodworking, leads into the expansive, sun-filled Kitchen and Family Room. Designed for entertaining, the formal Dining Room features a beautiful custom built-in and a charming bay window and connects to the Kitchen via a functional hallway ideal for use as a butler's pantry or bar. This hallway provides access to a combined mudroom/Laundry Room and Half Bath. The Kitchen and Family Room form the heart of the home, featuring a cozy gas fireplace, a six-burner Wolf range, and direct access to a private Deck and stone terrace-perfect for outdoor dining and summer gatherings.

52 Steeple View Ln, Woodbury

85 Woodlake Drive W, Woodbury
$920,000
2 Beds ⋅ 3 Baths ⋅ 934299 MLS
Elegant Condo Nestled on Picturesque Woodland Pond Converts Easily from 2 Bedrooms to 3 Bedrooms. Imagine enjoying your morning coffee and croissant while watching playful mallard ducks and green-wing teals flutter their feathers and paddle serenely past your kitchen and dining room windows. Then step through wide sliding glass doors onto a lovely landscaped patio that borders directly on the pond, at the center of which is a perpetual fountain whose spectacular spray rises high into the air and sparkles in the sun. Why is this condo especially prime? Because it one of the few units that actually overlook the Pond, and they rarely come on the market. So this is a unique opportunity to acquire an architecturally distinguished home in a peaceful pond-side community. In addition to unobstructed views of the pond from almost every room, its spacious dimensions, cozy living room fireplace, fully equipped modern kitchen, laundry room, attached 2-car garage, dedicated driveway, and easy convertibility to 3-bedroom home, will not only enrich your living experience but help preserve your home’s value as an investment in the years to come. Spacious bedrooms offer comfort, privacy, en suite bathrooms and walk-in closets. The bright main living area is perfect for entertaining , and the loft office space with vaulted ceilings and skylight can be transformed into a third bedroom. Residents enjoy top-notch amenities at the Woodland Pond clubhouse, including a Great Room, Party Room, Card Rooms, Gym, Sauna, Basketball Court, 3 Tennis Courts, Pool and Kiddie Pool. Ideally located near shopping, dining, and major highways, this condo combines exceptional views, versatility, and natural beauty in one inviting home.

85 Woodlake Drive W, Woodbury

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