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$8,995,000
5 Beds ⋅ 12 Baths ⋅ 1031340 MLS
A long driveway opens to a large courtyard with a classic fountain, revealing a magnificent Château-style Mansion on 2.03 acres of verdant property on a private cul-de-sac. Custom built for grand entertaining and everyday living, this incredible residence masterfully blends old-world European charm with modern luxury. A majestic 2-story entry foyer features a stunning domed-vaulted ceiling with a curved staircase, showcasing antiqued mirrored panels and an ornate wrought iron railing. Through a series of exquisite arches, the foyer leads to an expansive formal living room with a detailed ceiling and wall-to-wall windows as well as a palatial-sized dining room with a butler’s pantry that offers a wet bar and additional storage. The comfortable family room has a unique curved wall and a marble fireplace flanked by marble goddesses. Adjacent is a sitting room with a floor-to-ceiling built-in display wall and a cozy hexagonal built-in bay window seating area. Next door, an elegant study offers a productive place to work from home. A spectacular chef-inspired kitchen boasts a large breakfast area, dual islands, marble counters, a beautiful ILVE range with a show-stopping backsplash, Wolf, Miele and Sub-Zero appliances, plus an additional service kitchen to ensure effortless hosting. An opulent master suite retreat has a private sitting room with a fireplace, a convenient wet bar with refrigeration, 2 sets of French doors to front and rear balconies, and 2 walk-in closets – both with custom closet systems and one with a generous center island with storage – and features an incredible spa-like bath with a steam shower and a magnificent stand-alone soaking tub. All additional en-suite bedrooms are comfortable with ample walk-in closets and tastefully appointed baths with showers. The lower level is designed with a home gym, expansive recreation space, games area, raised stage, and handsome tufted leather doors leading to a state-of-the-art movie theater. An additional bonus space also offers a bedroom, closet, and a full bath with a shower. Flowing seamlessly outdoors, the lush, park-like property features an expansive bluestone terrace anchored by an outdoor fireplace and a gourmet summer kitchen equipped with a premium built-in grill, integrated refrigeration, and an artisanal pizza oven. Alongside the sparkling heated pool and large sun deck, a gorgeous cabana with a full bath and laundry provides an open yet covered space to relax, while dramatic torches illuminate the pool area at night, creating a resort-caliber experience. This exceptional smart home is complete with a Generac generator, central vacuum, Crestron security system, interior/exterior sound system, sprinkler system, radiant flooring, 3 fireplaces, fine millwork, and a 3-car garage. Just 27 miles from NYC, this French-inspired masterpiece of 5 bedrooms and 8 full baths/4 half baths, offers a tranquil retreat for the discerning buyer who appreciates a Gold Coast luxury lifestyle.

7 Covey Court, Upper Brookville
$3,799,000
5 Beds ⋅ 5 Baths ⋅ 1027379 MLS
Set on two flat, beautifully landscaped acres along a low-traffic street in Brookville, yet just minutes from major highways and shopping, this classic Colonial built in 1964 offers thoughtfully updated living space throughout. An extensive renovation touched nearly every corner of the home, from all new Marvin windows and doors to central air, updated heating, and a full repaint inside and out. The kitchen underwent its own complete transformation, emerging with high end appliances, a center island, and gas cooking, ideal for anyone who loves to cook and entertain. Three fireplaces warm the home throughout, found in the den, the living room, and the sunroom, where a new gas fireplace adds year round comfort. Upstairs, five bedrooms include a primary suite with a walk-in closet and an en suite bath featuring a soaking tub, stall shower, and double vanity, while a sixth bedroom was converted into a convenient laundry room. Three full baths and two half baths serve the home's living spaces, and a full unfinished basement offers ample storage or future potential. The three car garage, expanded from its original two car footprint, sits above with a second story that shares a wall with the primary suite. Comfort continues with three zone heating and air conditioning, a 400 amp electrical service, an automatic propane generator, and a Control4 smart home system managing sound, lighting, and video throughout. Outside, mature landscaping surrounds a brand new in-ground pool, a pergola, and an outdoor kitchen with a gas BBQ, perfect for warm weather gatherings. A new thirty year asphalt roof, new driveway, and updated sprinkler system round out a home where every major system and finish has been thoughtfully addressed. Colonial in style and scaled for gracious living, 15 Dogwood Hill offers a rare combination of space, setting, and easy access to everything Long Island's North Shore has to offer.

15 Dogwood Hill, Brookville
$1,200,000
2 Beds ⋅ 3 Baths ⋅ 1026338 MLS
Welcome to your dream coastal retreat! This custom built 2 bedroom , 3 bath contemporary home offers the perfect blend of modern luxury and effortless Long Island Sound side beach living. With private beach rights through the Pine-Howard Civic Association just steps from your front door you'll enjoy breathtaking views. Recent 2023 construction meticulously designed also includes a Fuji clean outside treatment system and is fully elevated to FEMA compliant standards for ultimate peace of mind. Walking distance to charming local shops, seaside dining & vibrant community spots. Step inside to an open concept layout designed to impress. Sleek living space with dramatic high beamed ceilings create an airy spacious feel. A cozy electric fireplace serves as the living areas stunning focal point. A gourmet kitchen beautifully appointed with custom cabinetry and stainless steel appliances. A luxurious spa inspired primary suite bathroom complete with whirlpool walk-in deep soaking tub. Private deck perfectly situated for hosting family gatherings and enjoying morning coffee.

6 Howard Road, Bayville
$3,295,000
5 Beds ⋅ 5 Baths ⋅ 1020514 MLS
Down a long, private, enchanting road canopied by mature trees, 17 Danton Lane is a modern 5-bedroom, 4.5-bath home that spans approximately 6,500 square feet on over 4 acres, in one of Lattingtown's most coveted beach enclaves, just a stroll from a private beach. A striking 2 story atrium foyer welcomes you in, with glass doors beckoning straight out to the backyard. The 2019 kitchen features large countertops, custom cabinetry, and Viking appliances, while a warm den offers a wet bar, dishwasher, and two wine refrigerators. The impressively large great room is designed for entertaining. On the other side of the house, the two-story primary suite includes a soaking tub, walk-in closets, and an upstairs office/den. The grounds were designed by Dubner and offer layered points of interest throughout, from a sparkling gunite pool with jacuzzi to a serene koi pond, creating a series of destinations to discover rather than a single view. Clean, contemporary design meets total privacy, lush surroundings, and private beach access on over 4 acres at 17 Danton Lane.

17 Danton Lane N, Locust Valley
$2,295,000
4 Beds ⋅ 6 Baths ⋅ 1016394 MLS
Diamond in the Rough. Oversized cedar shake Cape Cod style home, offers 4453SF of living space on 2 flat acres in Upper Brookville. Traditional Colonial layout features a two-story entry foyer flanked by a formal living room with wood burning fireplace and formal dining rooms, both with large picture windows. An open concept kitchen/great room w/ fireplace is the heart of the home, with high ceilings, reclaimed wood beams, a wall of windows and sliding doors, a chef's kitchen with 48" Wolf cooking and SubZ refrigeration and a large island with seating. Off the kitchen is the mud room entry from the rear or 2-car attached garage, laundry room, bedroom and full bath. On the south side of the house, on the 1st level, the primary suite offers a tray ceiling, multiple walk-in closets, an ensuite marble bath with double sinks, shower, windowed tub and private water closet AND a private office/sitting room/library. Upstairs contains 2 huge bedrooms, each with walk-in closets and private bath, with a common area loft space. The basement is the full footprint of the house and is unfinished, housing utilities and storage. The 2.5 car detached carriage house offers room for additional vehicles and has an unfinished room above. Plenty of room for expansion; just your imagination is required to bring this beauty back to life.

7 Locust Lane, Upper Brookville
$5,288,000
6 Beds ⋅ 7 Baths ⋅ 1010689 MLS
A Private Oasis in Upper Brookville. Timeless elegance prevails in this custom-built, majestic brick 6-bedroom, 6.5-bath manor home in Upper Brookville. Masterfully set at the end of a cul-de-sac, a private driveway leads to a spacious courtyard and impressive, stately residence set on 6 prime, serene acres. For a qualified buyer, this is an exceptional opportunity. Many many features include: a two-story entryway, a luxurious primary suite on the main level, a free-form inground heated gunite pool with a waterfall, a covered outdoor kitchen, and a 3-car garage. Luxurious living with hidden privacy and easy access.

7 Fairway Court, Upper Brookville
$938,000
4 Beds ⋅ 2 Baths ⋅ 1001116 MLS
Welcome to 28 Satinwood- This four-bedroom two bathroom move-in ready home is the one you’ve been waiting for! Situated in the beautiful village of Bayville in a non-flood zone, this thoughtfully updated raised ranch offers the best layout option for spreading out with nothing to do but move in! Upon entering, you’ll notice the freshly painted walls, beautiful gleaming hardwood floors with plenty of natural light. The kitchen has been completely remodeled with high ceilings, solid surface countertops, deep stainless steel farmhouse sink, new appliances, soft close cabinetry, gas for cooking, plenty of storage and sliding glass door adds both light and access to the large deck for ease of entertaining. Attention to detail is everywhere from the wood paneled doors, custom blinds, light fixtures and Elfa closet systems in every bedroom which make staying organized a breeze. The living room and dining room feature large windows, crown molding, hardwood floors, with exceptional flow for gatherings. Just down the gallery style hall you’ll find three of the four bedrooms; the primary bedroom which offers double door deep closets and windows on multiple walls to welcome the morning light while the other bedrooms are generous in size, offer custom closet systems and privacy. The main level bathroom provides a large vanity with storage, a tub/shower combo and ceramic tile floors. The lower-level offers the fourth bedroom with custom closet system, a fully remodeled bath that feels like a spa retreat with stone pebble floor shower and custom tilework--making this level a possible guest suite or ideal for multi-generational living, A spacious den boasts new floors, paint and lighting providing room for your home office, exercise area and space to relax, sliding doors lead to the large sunny backyard. A washer and dryer are located on this level as well. The garage provides space for two cars, additional storage and a workshop area while the side yard double gate allows for boat/trailer or RV parking. An added bonus rarely seen is washers and gas dryers are located on both floors of this move in ready home- No more carrying laundry up and down. The attic has new pull-down stairs and space to store many belongings. No detail has been looked over: generator, new central air, updated electrical, new hot water heater and professional landscaping are just a few of the upgrades that make this home stand out. Pack your bags and move in! Located in an established non-flood zone neighborhood in the village of Bayville that offers access to private village beaches, docks, pickleball, tennis courts and mooring rights. Locust Valley School District. Plenty of restaurants, activities with close proximity to shopping-everything that makes Bayville village living special.

28 Satinwood Road, Bayville
$4,000,000
4 Beds ⋅ 4 Baths ⋅ 955669 MLS
Move right into this stunning four-bedroom ranch residence set on 5.5 beautifully landscaped acres. Thoughtfully updated and impeccably maintained, this light-filled home offers an open-concept floor plan designed for today’s modern lifestyle. There is an updated one bedroom guest cottage and a separate office. Built on one level, the home showcases expansive floor-to-ceiling windows and doors that frame picturesque garden views and flood the interiors with natural light. The gracious living and dining areas are anchored by a striking double-sided stone fireplace, creating architectural interest and a warm, inviting ambiance. A sophisticated bar room with wine refrigeration and custom painted cabinetry enhances the cozy den, offering the perfect setting for entertaining. The expansive kitchen and family room serve as the heart of the home, featuring a dramatic double-height vaulted ceiling with loft above and seamless access to a side terrace ideal for outdoor dining and gatherings. Beautifully appointed with crisp white cabinetry, honed Absolute Black granite countertops, top-of-the-line appliances, and radiant heated floors, the kitchen flows effortlessly into the informal dining area and family room, complete with a raised-hearth stone fireplace. Additional highlights include pristine condition throughout, Newly painted and redone guest quarters, separate living and dining rooms, and a separate hot water heater., New generator, new gas line (2025), House newly painted and redecorated and grounds re landscaped. The Property in Spring is filled with an abundance of color with the Hellebores, Azaleas, Rhododendron. It is private and magical.

343 Chicken Valley Road, Upper Brookville
$3,850,000
6 Beds ⋅ 6 Baths ⋅ 973588 MLS
Tucked away on a serene private road just minutes from the storybook charm of Locust Valley, this Mediterranean-style Colonial is a true estate of distinction. Sited on 5+ pristine acres, seamlessly blends classic elegance with modern luxury. Designed with both grandeur and comfort in mind, the home features two gracious primary suites on the main level, a total of 6 spacious bedrooms, 5 full bathrooms, and one half bath. Soaring 10-foot ceilings enhance the sense of openness throughout, while rich oak hardwood floors provide warmth and sophistication in every room. The heart of the home is a massive chef’s kitchen, thoughtfully appointed for both entertaining and everyday living. A timeless oak-paneled library offers a refined retreat for work or leisure. The layout is perfectly made for making entertaining a seamless, enjoyable experience. Recently renovated, upstairs bathrooms, along with brand new HVAC systems, and a newly constructed three-car garage, ensure turnkey ease and modern comfort. Full partially finished basement, with walkout to outside. "The Last of the Mohicans" on a highly desirable private road in Matinecock, this extraordinary property offers rare privacy and elegance in one of Long Island’s most coveted enclaves. Close proximity to LIRR (train), renowned golf courses, and schools makes this a desired location. A truly unique offering that must be seen to be appreciated.

406 Duck Pond, Locust Valley
$8,995,000
6 Beds ⋅ 10 Baths ⋅ 970669 MLS
Maison Blanche: An Architectural Icon in Upper Brookville Experience the pinnacle of ultra-modern luxury at 31 Chestnut Hill Drive. Set on five flat, private acres at the crest of a premier cul-de-sac, this architectural sanctuary was originally designed by the renowned architect Gary Gallagher and redesigned by award-winning FAIA architect Stuart Narofsky, leading to an extensively renovated (2023–2026) masterpiece. The residence features six bedrooms with en-suite bathrooms, four additional half-baths, to include an expansive first-floor primary suite. Architectural highlights include two custom floating staircases with glass railings, porcelain and white oak floors, and frameless full-bodied Belldinni doors. The chef’s kitchens in the main and guest houses are equipped with Wi-Fi-controlled Thermador appliances and specialty quartz islands. Uniquely designed for wellness and entertainment, the second-floor features 3 bedrooms and a private gym and Finnish sauna, while the lower level boasts a Dolby-Atmos theater, wine tasting room, a yoga/massage spa, and a wet bar. Outside, a heated saline pool and spa are framed by a porcelain patio and an unobstructing glass railing, and an outdoor wet kitchen. App-controlled for the modern age, the estate features smart management of the custom steel entry gate, five-zone HVAC, motorized shades, security, and a whole-house generator. This is the new standard of Gold Coast living.

31 Chestnut Hill Drive, Upper Brookville
$2,895,000
4 Beds ⋅ 5 Baths ⋅ 967360 MLS
UPPER BROOKVILLE. Privately set behind sweeping lawns on over two acres in the Village of Upper Brookville, this elegant North Shore residence offers the privacy, scale, and timeless character synonymous with Gold Coast estate living. The home features 4 bedrooms, with primary suite on the main, and 3 full and 2 half baths, along with sun-filled living spaces, hardwood and tiled (radiant heated) floors, where seen, and classic architectural details throughout. A gracious entry leads to beautifully proportioned interiors designed for both everyday comfort and sophisticated entertaining. The formal living room with fireplace flows seamlessly into the dining room and adjoining sun room, creating an inviting setting for gatherings large or small. At the heart of the home, the chef’s kitchen features custom cabinetry, stone countertops, and a generous center island, opening naturally to the main living areas. The first-floor primary suite provides a private retreat complete with a walk in closet and a beautifully appointed bath with soaking tub and oversized shower. Additional bedroom/library on the first floor offers the perfect space for a home office or quiet relaxation. The second level includes additional bedrooms and bath, while the finished lower level offers exceptional entertaining amenities including a home theater, wine cellar, and bar/kitchenette. Outdoors, the property features expansive lawns and patios, mature landscaping, koi pond, fire pit, and an inground heated Gunite pool with detached guest/pool house (featuring full bath, kitchenette, living room with fireplace, and rec area), and 2 outdoor BBQ spaces, creating an ideal setting for summer entertaining and weekend gatherings. Conveniently located to world-class golf courses, equestrian estates, yacht clubs, and the charming villages of Locust Valley, Roslyn, and Manhasset, with Manhattan just a short commute away. A rare opportunity to enjoy refined estate living in the heart of Upper Brookville. Additional features: whole house generator, exterior lighting throughout, built in speakers throughout interior and exterior, 2 car attached heated garage, cul-de-sac location, and more.

1017 Friendly Road, Upper Brookville
$3,695,000
7 Beds ⋅ 7 Baths ⋅ 959529 MLS
Exceptionally built all brick colonial on 4 acres with sparkling pool is ready for Summer occupancy. Located in the Village of Lattingtown within the Lands End community, a private enclave of beautiful homes on larger property sizes in Locust Valley, NY on the North Shore of Long Island. Custom built to the highest standards of craftsmanship and design. The grand all brick colonial is introduced by a long paver driveway leading to an elegant courtyard and portico entry. Inside, timeless architecture and abundant natural light define the spacious rooms. A sweeping double bridal staircase makes an immediate statement in the foyer, while a magnificent double height great room, richly appointment den with fireplace, formal dining room and refined library/study each offer comfortable and sophisticated living spaces. The updated chef's kitchen with new appliances and breakfast area overlook the expansive patios and manicured grounds. The residence offers exceptional versatility with two luxurious primary bedroom suite options, 1st floor and 2nd floor, along with a private guest wing, totaling 7 bedrooms and 6.5 baths in the main house. With resort-style living and entertaining in mind, the property features a spectacular swimming pool and spa, stunning waterfall, complemented by a fully equipped pool house providing a serene resort style retreat. Sports Court on site is a bonus feature for playing basketball, tennis and more. Professional landscaping ensures privacy and beauty, while multiple terraces and gathering spaces invite seamless indoor-outdoor living. Excellent condition hardscape and park-like grounds. A separate structure 4 car garage with heated finished storage space above adds convenience and flexibility. Ideally located in Locust Valley, widely regarded as the crown jewel of the historic Gold Coast - this magnificent estate offers close proximity to Manhattan while enjoying the very best of North Shore living, including nearby beaches, renowned arboretums, Planting Fields State Park, boutique shopping, acclaimed dining, premier golf, tennis and boating clubs and a close sense of community. Locust Valley School District and nearby private schools including Friends Academy and Portledge, this extraordinary property defines North Shore luxury and offers a rare opportunity to experience refined living at this finest.

11 Danton Lane N, Lattingtown
$7,950,000
6 Beds ⋅ 9 Baths ⋅ 953633 MLS
Introducing a newly constructed custom Brookville Colonial crowned with a stunning slate roof, offering an extraordinary blend of classic architecture and elevated designer finishes. Privately set behind an electric gate on over 2.53 fully landscaped acres, this exceptional estate, constructed in 2020, has been thoughtfully designed for both grand-scale entertaining and refined everyday living. A long, stone driveway leads to the residence, accented by elegant black-trimmed windows, courtyard entrance and timeless curb appeal. This bespoke home features six generously sized bedrooms, seven full bathrooms, and two half baths, complemented by soaring ceilings and exquisite millwork throughout. A gracious foyer creates an impressive first impression, opening to sophisticated formal spaces including a sunken living room with a custom fireplace, and a refined parlor or music room adorned with elegant stone floors and dramatic walls of glass. Rich herringbone hardwood flooring flows seamlessly throughout the home, enhancing its timeless elegance. A formal dining room and private office, each with a fireplace, complete the main entertaining areas. At the heart of the home is a spectacular double-island gourmet kitchen, impeccably outfitted for the most discerning chef and ideal for hosting. The kitchen features a wet bar, oversized pantry, and flows effortlessly into a warm and inviting den. A first-floor junior primary suite with a private full bath offers flexibility, with direct access to the attached 2+ car garage. A thoughtfully designed laundry and mudroom area includes a built-in dog wash for added convenience. The primary suite is a true private retreat, showcasing cathedral ceilings, a fireplace with an adjoining lounge area, a spacious custom walk-in dressing room, and a spa-inspired bath with a soaking tub and oversized shower. A private rooftop terrace/sundeck overlooks the serene backyard, creating a peaceful escape. All additional bedrooms are generously sized and feature beautifully appointed ensuite baths, all of which have radiant floor heating. The fully finished lower level further elevates the lifestyle experience, offering a state-of-the-art media room and theater, a large matted gym, and a luxurious spa bathroom with a steam shower. Outdoors, the property is designed for resort-style living, featuring an in-ground pool, spa with pergola, expansive patios, and meticulously manicured grounds that provide privacy, scale, and elegance. This exceptional estate presents a rare opportunity to own a newly built, turnkey residence of enduring quality - crafted for those who value sophistication, comfort, and distinction - located within the highly regarded Locust Valley Central School District.

30 Wood Acres Road, Brookville
$5,495,000
6 Beds ⋅ 7 Baths ⋅ 949662 MLS
Set on two private acres in the heart of Brookville and located within the Locust Valley School District, 63 Fruitledge Road offers refined luxury living on Long Island’s prestigious Gold Coast. This newly completed 6,880 Sq ft residence features a striking modern Colonial exterior with expansive windows and 10-foot ceilings throughout, creating an airy, light-filled atmosphere and large-scale rooms ideal for both everyday living and entertaining. A grand foyer introduces the home’s elegant flow. The formal living room includes a fully equipped custom marble wet bar, while the open-concept den is framed by floor-to-ceiling windows overlooking the backyard and anchored by a marble fireplace.The custom kitchen opens seamlessly to the formal dining room and is complimented by thoughtful storage cabinetry, a large center island, Gaggenau gas appliances, double Bosch dishwashers, and a Sub-Zero refrigerator/freezer. Upstairs, all five bedrooms are en suite, offering privacy and comfort for guests alike. The extra-large primary suite serves as a private retreat, featuring dual outfitted custom walk-in closets and a luxurious marble bath with a steam shower, soaking tub, and two vanities. A spacious laundry room is conveniently located on this level. A well-designed service area beyond the kitchen includes a mudroom, a walk-in pantry, a full bath, and convenient access to the three-car garage, back staircase, and steps leading to the basement. The main level also features a generously sized bedroom, ideal for guests or extended stays. Radiant heated floors are featured in all bathrooms and the mudroom. The outdoor space is equally impressive, featuring a heated 40' x 20' Gunite saltwater pool, paver patio, and outdoor kitchen—perfect for entertaining or enjoying the serene, private grounds.

63 Fruitledge Road, Brookville
$5,585,000
9 Beds ⋅ 12 Baths ⋅ 885874 MLS
Welcome to GRAY HORSE FARM - Just Updated & Renovated for 2025 luxury living! Recently transformed with a gut-renovated Top of the line chef's kitchen with new cabinets, countertops, backsplash, floor, and high-end appliances. There are six new designer bathrooms, all-new recessed lighting throughout, upgraded 800-AMP electric and utility systems. This grand estate seamlessly blends timeless elegance with modern comforts. A truly iconic Georgian estate nestled in the heart of Upper Brookville, this 17,587 square feet of total living space, this sprawling residence features 9 bedrooms, 9.555+ bathrooms, 10 wood-burning fireplaces, and exquisite architectural details, including vintage millwork, antique hand-painted wallpaper, and Samuel Yellin wrought-iron gates from the JP Morgan estate. Designed in 1924 by renowned architect James W. O’Connor and landscape architect Robert Ludlow Fowler, Gray Horse Farm is where classic architecture meets nearly 9 acres of pristine, equestrian-ready grounds. Perfectly suited for multigenerational living, the estate includes three separate guest/staff quarters (two 1-bedrooms and one 3-bedroom), offering privacy while staying connected. For those who love to entertain and enjoy the outdoors, the estate features a 20' x 55' heated saltwater pool with a pool house that's fully equipped, tennis and basketball courts, and a secret meditation garden you don't want to miss. For the car enthusiast there's a 7-car garage. Equestrian enthusiasts will appreciate the 3-stall stable, multiple paddocks, and run-in horse shed, all designed for top-tier country living. Additional highlights include a whole-house generator, —all just 27 miles from Manhattan. Whether you're seeking a premier equestrian retreat or an expansive generational compound, Gray Horse Farm delivers an unmatched lifestyle of luxury, privacy, and prestige. A rare offering close to top universities,marinas, beaches, golf, museums and americana shopping!

60 Piping Rock Road, Upper Brookville

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.