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$6,999,000
7 Beds ⋅ 9 Baths ⋅ 1021590 MLS
Old Brookville | Welcome to 3 Valentine Farm Court, where timeless architecture, exceptional craftsmanship, and an unmatched collection of luxury amenities define one of the North Shore's most impressive private estates. Positioned behind double iron gates at the end of a secluded cul-de-sac, this stately brick center hall colonial is situated on more than three meticulously landscaped acres, combining remarkable privacy with an extraordinary level of recreation and entertaining amenities. The residence is introduced by a spectacular two-story domed foyer showcasing a sparkling chandelier, intricate hand-painted ceiling details, and extensive custom millwork carried throughout every level of the home. Formal and informal living spaces are thoughtfully arranged, including an expansive formal living room, richly appointed mahogany library, inviting family room with one of three wood-burning fireplaces, formal dining room, powder room, and a spacious first-floor en-suite bedroom with separate exterior access. The custom kitchen is appointed with premium gas appliances, custom cabinetry, a center island with seating, an adjoining breakfast area, and an expansive butler's pantry connecting directly to the formal dining room. Extending from the main level, an elevated terrace with a built-in outdoor kitchen overlooks the estate grounds and pool complex below. The second level features five bedroom suites, each with their own full bathroom. Occupying its own wing of the home, the primary suite includes a private balcony overlooking the property, separate sitting room, two oversized walk-in closets, and an expansive en-suite bathroom with dual vanities and a jetted soaking tub. Designed as an exceptional recreational and entertaining space, the lower level features a custom wet bar, expansive gathering areas, a fully equipped fitness center, additional bedroom and full bathroom, oversized laundry room, and a below-grade indoor sports court with min. 15-foot ceilings—a rarely available amenity in residential construction. The outdoor amenities are equally impressive. The resort-inspired grounds are centered around an oversized gunite swimming pool with an integrated spa and water features, surrounded by expansive patios and mature landscaping. A fully equipped pool house includes a full bathroom, laundry facilities, and an indoor kitchen with a built-in grill opening directly onto the pool terrace. Completing the estate is a full-size sports court configured for both tennis and basketball, along with an oversized three-car garage equipped with vehicle lifts offering additional space for the car enthusiast. Representing an exceptional combination of scale, craftsmanship, and amenities on more than three private acres, 3 Valentine Farm Court presents a rare opportunity within one of the North Shore's most distinguished settings.

3 Valentine Farm Court, Old Brookville
$1,495,000
4 Beds ⋅ 4 Baths ⋅ 1023642 MLS
New Construction in North Shore School District: Enjoy the perfect home with 4 bedrooms, 3.5 bathrooms, a mudroom, and a one car garage. Situated on a level 60’ x 100’ property, on a quiet cul-de-sac, this home provides a lovely primary suite with tray ceilings, two spacious closets and a primary bath featuring a double sink vanity and a soaker tub. The kitchen boasts quality finishes with Fabuwood cabinets, under cabinet lighting, quartz countertops, a 36” gas Bertazzoni range and a large center island including a wine cooler. You can finish the full basement which already has 10’ ceilings and outside entrance. Don’t miss this opportunity to make this dream home yours!

9 First Street, Glenwood Landing
$2,695,000
2 Beds ⋅ 3 Baths ⋅ 1021582 MLS
One of the most unique luxury condos at The Residences at Glen Harbor with the largest patio over 1,200 that fully wraps around and is ideally situated on the first floor with panoramic waterfront views of the harbor and LI Sound. Unit #101 is being offered fully furnished as an option allowing for immediate enjoyment on day one with many upgrades made too, including custom entertainment built-ins, bedroom closets and a functional in unit mud room with storage, plus laundry. In addition, this particular condo also comes with a private secure storage space inside the building located just by the unit. 2 parking spaces in the garage. This newly listed condo is spacious and a beautiful open floor plan. The kitchen has two islands now, quartz countertops featuring Sub-Zero and Wolf appliances. Dining Room open to Living Room with walls of windows bringing in the natural light and looking out to the direct waterfront view. Modern and effortless living at this luxury condo building full of amenities. The primary bedroom suite offers a serene oasis overlooking the water, custom built-in closets throughout and the two walk-in closets, porcelain spa bathroom. The guest bedroom was created to become an en-suite experience, very private and comfortable. The Residences at Glen Harbor delivers a luxury waterfront lifestyle with exceptional amenities including 24 hour doorman and concierge services, welcome lobby, clubhouse lounge, coffee bar, two fitness centers including a cardio room and free weight room, resort-style heated swimming pool outside, pool house pavilion, sun decks, bbq area and so much more. Full building generator. Residents also enjoy a scenic boardwalk along the waterfront, unobstructed views of Hempstead Harbor and the Long Island Sound, beautifully landscaped grounds, and a private community atmosphere. Conveniently located near shopping, dining, transportation, and North Shore conveniences. Fully furnished option. Move in immediately and enjoy, just bring your toothbrush.

10 Shore Road Unit #101, Glenwood Landing
$2,849,000
5 Beds ⋅ 4 Baths ⋅ 1019591 MLS
ROSLYN HARBOR. Beautifully positioned on a private, park-like acre in the heart of Roslyn Harbor, this exquisitely renovated ranch seamlessly blends sophisticated design with the ease of luxurious single-level living. Completely reimagined in 2017, meticulously kept and renovated again in 2022 by the current owners, this exceptional residence offers 5 bedrooms, 3 full and 1 half baths, and an expansive open-concept floor plan thoughtfully designed for both elegant entertaining and everyday comfort. Bathed in natural light from 15 strategically placed skylights and expansive walls of glass, the home's sun-drenched interiors create a seamless connection between indoor and outdoor living. Refined architectural details, generous proportions, and impeccable craftsmanship are showcased throughout. The formal living room, anchored by a fireplace, is thoughtfully defined by a custom wood bench that creates a subtle transition into the designer kitchen. A true showpiece, the kitchen features stainless steel appliances, quartz countertops, custom cabinetry, and a dramatic suspended architectural truss lighting installation with museum-quality adjustable LED illumination. The adjoining formal dining room is equally impressive, appointed with custom built-in cabinetry, a Sub-Zero wine cooler, and floor-to-ceiling windows overlooking the picturesque grounds. The inviting family room, complete with a second fireplace and direct access to the outdoor patio, provides the perfect setting for effortless indoor-outdoor living. Privately situated, the luxurious primary suite serves as a tranquil retreat, featuring two walk-in closets—including one with a dedicated vanity—and a spa-inspired bath appointed with radiant heated floors, a double vanity, bidet, private water closet, and designer finishes. Four additional bedrooms, including one en-suite, a beautifully appointed full bath, powder room, and a spacious laundry/mudroom complete the home's thoughtfully designed layout. Outside, the beautifully manicured grounds offer exceptional privacy and an idyllic backdrop for entertaining and relaxation. A rare offering that pairs timeless architecture with contemporary sophistication, this move-in-ready Roslyn Harbor residence presents an extraordinary opportunity to enjoy refined North Shore living just moments from shopping, fine dining, golf courses, country clubs, and major parkways.

3 Engineers Road, Roslyn Harbor
$4,795,999
11 Beds ⋅ 14 Baths ⋅ 1016829 MLS
A truly extraordinary opportunity to create one of Brookville's most distinguished private estates. Nestled on an expansive 15-acre parcel in the prestigious Village of Old Brookville, this remarkable property offers an unparalleled setting on one of the area's most coveted and desirable streets. Plans envision a magnificent 22,000-square-foot luxury residence thoughtfully designed to blend timeless elegance with modern sophistication. Surrounded by mature landscaping and serene natural beauty, the estate offers exceptional privacy while remaining conveniently located near renowned schools, country clubs, fine dining, and major transportation routes. A picturesque private pond serves as the centerpiece of the grounds, creating a tranquil and captivating backdrop for the future residence. The vast acreage presents limitless possibilities for world-class amenities, including formal gardens, resort-style outdoor living spaces, recreational facilities, and equestrian pursuits. Rarely does an offering of this caliber become available—a unique chance to build a legacy estate tailored to your vision in one of Long Island's most exclusive enclaves. An exceptional canvas upon which to create a truly iconic residence

1 Penny Pond Court, Old Brookville
$21,500,000
10 Beds ⋅ 10 Baths ⋅ 1010319 MLS
Steeped in the grandeur of Long Island's celebrated Gold Coast, this extraordinary 33+ acre equestrian estate formally named 'Westward' presents a rare opportunity to acquire a significant piece of North Shore history. Privately nestled amid rolling pastures, mature woodlands, and formal gardens, the estate seamlessly blends timeless architectural elegance with an unparalleled country lifestyle just moments from New York City. Originally commissioned in 1924 for noted industrialist and financier Benjamin Brewster Jennings - President and Chairman of Socony-Mobil and a prominent figure in New York's financial and corporate circles - this Georgian Revival brick residence with a cascading slate roof was masterfully designed by renowned architect Walter B. Chambers. The estate's distinguished landscape plan was created by legendary landscape architect Ellen Biddle Shipman, whose formal gardens and thoughtfully designed grounds continue to define the property's enduring beauty. Approached by a long, tree-lined drive framed by classic stone walls, the stately residence commands a setting of exceptional privacy and serenity. Encompassing three full levels of living space, the home is distinguished by grand entertaining rooms, soaring proportions, multiple wood-burning fireplaces, graceful arched windows, leaded-glass details, and an abundance of natural light. A gracious entrance vestibule opens to a sweeping curved staircase, while expansive formal living and dining rooms provide an elegant backdrop for entertaining on any scale. The 10 bedroom, 9.5 bathroom primary residence also features a spacious eat-in kitchen, indoor spa pool, vast slate patios and an outdoor swimming pool with cabana set against picturesque grounds, providing an idyllic backdrop for outdoor enjoyment. For equestrian enthusiasts, the property offers a turnkey horse facility. The grounds include a well-maintained main barn, four run-in sheds (equipped with stalls, water, and electricity), a hot walker, extensive paddocks, and open acreage ideal for riding and grazing. Additionally, this unmatched property includes charming gatehouse cottages, staff apartments, and multiple ancillary structures, most of which have been recently renovated, creating flexibility for guests, caretakers, or income-producing opportunities. Located within one of the North Shore's most prestigious and historically significant communities, the estate enjoys close proximity to Long Island Sound beaches, renowned equestrian facilities, and some of the region's finest private clubs and golf courses. Zoned within the esteemed North Shore Central School District. Rarely does a property of this caliber come to market - offering a remarkable combination of provenance, architectural distinction, equestrian amenities, acreage, and development potential. A legacy estate of exceptional character and enduring significance, representing the very essence of North Shore country living.

97 Pound Hollow Road, Old Brookville
$5,498,000
7 Beds ⋅ 8 Baths ⋅ 1009813 MLS
Nestled on approximately 5 landscaped acres in Old Brookville, this distinguished estate offers exceptional space, privacy, and classic Gold Coast character. The property includes a stately main residence, a separate 3-bedroom guest cottage, and a pool house, providing flexible living and entertaining opportunities. The main residence offers approximately 5,764 square feet of living space with 7 bedrooms, soaring ceilings, hardwood floors, and elegant French arched windows that bring abundant natural light throughout the home. Expansive interiors overlook manicured grounds, gardens, and open scenic views. Recently renovated bathrooms blend modern updates with timeless design, while generously sized living areas provide comfort and functionality. The beautifully maintained grounds showcase seasonal landscapes and mature plantings, creating a serene setting year-round. Accessed through a gated entrance and private drive, this exceptional estate presents a rare opportunity to own a significant property in the desirable Village of Old Brookville.

952 Cedar Swamp, Old Brookville
$749,888
3 Beds ⋅ 1 Baths ⋅ 1002991 MLS
Charming one-level ranch offering easy living and modern updates! This well-maintained home features three spacious bedrooms, a beautifully updated full bath, and a brand-new eat-in kitchen perfect for everyday living and entertaining. The inviting living room includes a door leading directly to the backyard, creating a seamless indoor-outdoor flow. Additional highlights include a versatile bonus room ideal for a home office, den, plus a one-car attached garage for convenience. Nestled on a quiet, tree-lined street with low taxes, this home is perfectly located close to downtown, beaches, shopping, and restaurants. A wonderful opportunity for comfortable and convenient living! North Shore School District with a Glen Cove address.

12 Ronan Road, Glen Cove
$5,499,000
9 Beds ⋅ 8 Baths ⋅ 1005247 MLS
Set on 3.32 meticulously landscaped acres, this sophisticated and elegant Gold Coast jewel is a true luxury retreat. The home was designed by esteemed early 20th-century architect Mott B. Schmidt, who was highly regarded for his grand homes. A grand entrance welcomes guests, framed by stately arched trees that line the long, circular driveway. Inside, the richly paneled foyer and wide pegged oak floors set the stage for exquisite architectural details, including a sweeping staircase and intricate custom millwork. The first floor offers a seamless blend of grandeur and comfort. The magnificent living room and banquet-sized dining room both feature elegant fireplaces, while the gourmet kitchen boasts a spacious center island and a bright breakfast room. A butler’s pantry adds convenience, and the library, adorned with built-in bookcases and a fireplace, offers a cozy retreat. Additional highlights include a sunroom, two en suite guest bedrooms, a first-floor washer/dryer, and a powder room. Oversized windows throughout the home provide breathtaking views of the lush grounds. The expansive primary suite is a private sanctuary, complete with a fireplace, spa-like bath, dressing area, and a large balcony overlooking the manicured gardens. This level also features four additional bedrooms with two Jack-and-Jill baths, two additional fireplaces, a gracious hall bath, a gym/bedroom, an office/bedroom, and a second-floor laundry room. The lower level offers an abundance of recreational space, including a playroom, arts and crafts area, and a full bath. The exquisitely landscaped grounds provide something for everyone, offering endless opportunities for relaxation and entertainment. The sunken gardens, originally designed by renowned landscape architect Robert Ludlow Fowler Jr., are a marvel to behold. They gracefully lead the way to a serene 20x50 saltwater gunite pool that is complemented by a spacious, elegant pool house. Sports enthusiasts will appreciate the lighted clay tennis court and a heated, enclosed outdoor structure, perfect for squash or basketball. Adding to the estate’s appeal, a charming three-bedroom, two-bath guest cottage provides comfortable accommodations, while a three-car heated garage with a separate workroom ensures ample space for vehicles and storage. This extraordinary estate is a timeless masterpiece inside and out, seamlessly blending historic charm with modern refinement.

8 Stonegate Lane, Old Brookville
$899,000
2 Beds ⋅ 4 Baths ⋅ 996990 MLS
FULLY AVAILABLE! Southern-facing, spacious, light-filled, and private townhouse featuring sleek black hardwood flooring throughout. The open entry foyer with cathedral ceilings leads to a sunlit living room with sliders to the back deck. Additional highlights include a formal dining room, an eat-in kitchen with quartz countertops and matching backsplash, a kitchen island with extra storage, a laundry area with pantry storage, a powder room, and access to a one-car garage. Upstairs, the second floor offers a primary bedroom with a Zen-style retreat bathroom and a generous closet area. You'll also find a second bedroom, an additional full bathroom, and a den/office space with access to the upper deck. The full basement features an open layout, a full bathroom, and an egress window. Located in the award winning North Shore school district, and a short distance from schools, restaurants, library and the Glen Head LIRR!

40 Cedar Lane N Unit #40, Glen Head
$6,850,000
7 Beds ⋅ 10 Baths ⋅ 991638 MLS
Set behind private gates in the prestigious Estates at Greenfield, this stately brick Georgian Colonial is perfectly positioned on three + magnificently landscaped acres, offering an exceptional blend of timeless architecture and resort-style living. A gracious approach leads to a generous courtyard, creating a striking first impression and a true sense of arrival. Inside, a dramatic two-story center hall marble foyer showcases a sweeping wrought iron circular staircase and exquisite, detailed millwork that sets the tone for the home’s refined interiors. The formal living room is both elegant and inviting, complete with a custom built-in bar and hardwood floors while the generous dining room is perfectly suited for grand entertaining. A warm and inviting den with a fireplace sits just off the chef’s kitchen and sunlit breakfast nook, creating an ideal flow for everyday living. A richly appointed home office features its own fireplace, custom built-in shelving, and a convenient half bath. The first floor is further enhanced by a private ensuite bedroom, perfect for guests or extended family. The second level offers a luxurious primary en-suite retreat with a fireplace, a gracious sitting room, and multiple custom-fitted closets. The spa-like marble bathroom adds to the sense of indulgence. Four additional ensuite bedrooms provide comfort and privacy, while a fabulous bonus room offers flexibility as a second den, media lounge, or computer room. The lower level has been thoughtfully designed for recreation and relaxation, featuring a game room, media area, gym, and abundant storage. Outdoors, the property is truly extraordinary—lush, expansive, and beautifully curated with mature specimen trees that provide both privacy and natural beauty. Designed for both relaxation and recreation, the grounds include a sparkling pool and hot tub, a full-service cabana, and a fully equipped outdoor kitchen ideal for seamless entertaining. A sports court and playground complete this exceptional offering. The property is simply divine—an all-encompassing retreat in The Estates at Greenfield, where every amenity has been thoughtfully curated, offering a lifestyle so complete there is truly no reason to ever leave home.

6 Evergreen Way, Old Brookville
$3,299,888
6 Beds ⋅ 6 Baths ⋅ 977675 MLS
Welcome to a rare opportunity to own a fully renovated and extended estate—rebuilt from the studs up and reimagined for modern luxury in the heart of one of Long Island’s most coveted neighborhoods. Set on a beautifully manicured 2 acre lot, this 6-bedroom, 5.5-bathroom smart residence combines sophisticated design, premium finishes, and cutting-edge amenities, offering a seamless blend of elegance. Every inch of the home reflects quality and intention—from the radiant heated floors throughout the entire main level and every bathroom to the sleek, designer fixtures and finishes throughout. The gracious first floor features a private guest suite with a separate entrance, ideal for extended family and guests. The chef’s kitchen is the true centerpiece—a culinary dream outfitted with a massive center island, top-tier stainless steel appliances, including a 48” Bertazzoni induction range with double ovens, oversized refrigerator and freezer, dual dishwashers, custom cabinetry, beverage drawers, and thoughtful built-ins—all designed to inspire both intimate dinners and large-scale entertaining. The second floor is home to a luxurious primary suite with a spa-inspired en-suite bath, radiant heated floors, oversized closet, and tranquil views of the property. Three additional spacious bedrooms upstairs offer generous closets, and large windows that flood the rooms with natural light. With a dedicated second-floor laundry area, convenience meets everyday function for busy households. The fully finished basement features its own private exterior entrance and offers an abundance of versatile space, including a wine cellar, gym, recreation, full laundry room, and more— The home's brand-new exterior features include a new roof, striking black energy-efficient windows, and a large Trex deck that opens from the kitchen to your own private oasis complete with an in-ground pool. Every system has been updated—new electrical, plumbing, floors, HVAC, and insulation—ensuring true turnkey luxury living. This is more than a home—it's a statement. A rare offering of timeless craftsmanship and modern design in one of the most distinguished enclaves.

33 High Farms Road, Old Brookville
$2,699,900
5 Beds ⋅ 4 Baths ⋅ 974758 MLS
Stunning Old Brookville Estate on 2 Acres with Pool & Outdoor Oasis Welcome to this exquisite 5-bedroom, 4-bathroom home nestled on 2 acres of beautifully landscaped property in the prestigious area of Old Brookville. This elegant residence offers the perfect blend of luxury, comfort, and privacy. Step inside to discover spacious living areas filled with natural light, including a grand living room with a cozy fireplace, a formal dining room, and a gourmet kitchen. The primary suite is a private retreat, complete with a spa-like en-suite bathroom. The fully finished basement is an entertainer’s dream, featuring a custom bar and ample space for gatherings. Outdoors, enjoy a serene backyard paradise with an in-ground pool, a charming gazebo, and a spacious patio—perfect for relaxing or entertaining. This exceptional property offers a rare opportunity to own a piece of paradise in one of Long Island’s most desirable locations. Don’t miss out on this remarkable home!

Glen Head
$1,850,000
5 Beds ⋅ 4 Baths ⋅ 943383 MLS
This one-of-a-kind home combines modern style, thoughtful design, and custom craftsmanship throughout. The main level features a welcoming entry foyer, a formal living room with fireplace, dining room, and a spacious, open kitchen with a wood-burning stone fireplace. A main-level bedroom with full bath, powder room, and family room complete the floor. Upstairs, the primary suite is a modern retreat with double sinks, a spa-style bathtub, and a large walk-in shower. Two additional bedrooms share a Jack-and-Jill bath and a fifth bedroom in the loft area. Custom wooden staircases and design elements give the home warmth and character. The fully finished basement includes expansive storage and a laundry area. Modern amenities abound: 3-zone central heat and air, radiant heat in first-floor living areas, solar panels with an extra battery functioning as a generator, indoor and outdoor cameras, tesla charger, and a speaker system in the living room, dining room, kitchen, and primary bath. Outside, enjoy a putting green, Japanese style dry garden, and turf yard- all low-maintenance for easy living. The expansive driveway accommodates multiple cars. Every inch of this home was thoughtfully customized, creating a modern, stylish space that’s both functional and cool, ideal for today’s lifestyle.

3 Maple Street, Glenwood Landing
$3,499,000
6 Beds ⋅ 9 Baths ⋅ 921399 MLS
Welcome to 12 Ridge Ct, located in the heart of Old Brookville in the Brookville Meadows. This is your window of opportunity to live in the Gold Coast on 3.4 acres of flat land. From the moment you turn on to the tree-lined street (White Gate Dr.) entering Brookville Meadows, you will feel the caliber of luxury you are about to enter. This home boasts over 7,800 sq feet, the open layout will give you endless possibilities. Enjoy your very own private elevator that goes to every level of the house. This estate offers 6 bedrooms, 7 full baths, and 2 half baths. Step inside and experience the grand scale of the first floor, where the expansive Great Room serves as the heart of the home. Featuring a striking two-sided fireplace, it seamlessly flows into a cozy Family Room, perfect for gatherings or quiet evenings. The Primary Suite occupies its own private wing on the main level with a guest powder room and offers a serene retreat, complete with a sitting area and fireplace, two full bathrooms, two full closets, and an adjoining bedroom with elegant French doors — ideal as a nursery, home office, or additional private suite. On the opposite wing, a private entrance leads to a sun-drenched, oversized Eat-In Kitchen, featuring Marvin windows that flood the space with natural light, Sub-Zero refrigerator, and two Bosh dishwashers. This space opens directly into a formal Dining Room, ideal for hosting. Nearby, you'll find a spacious Guest Ensuite, a convenient Laundry Room, and interior access to a 4-car garage. A hallway from the garage leads to both the backyard and the enormous, partially finished full basement — the full footprint of the home, offering endless potential. There are two full bathrooms with direct access to the pool. The second floor features three large bedrooms. Two share a Jack & Jill style full bathroom, while the third enjoys its own ensuite bath and a private balcony with stunning views of the backyard. An additional oversized bonus room offers incredible flexibility — ideal for a playroom, gym, media room, or extra bedroom. Step outside into your resort-style oasis. The beautifully renovated in-ground gunite pool is the centerpiece of this entertainer’s dream yard. A poolside kitchenette, a charming gazebo, and a pristine tennis court complete the scene — perfect for hosting, relaxing, or simply enjoying the peace and privacy of your own estate.

12 Ridge Court, Old Brookville
$5,490,000
6 Beds ⋅ 6 Baths ⋅ 845880 MLS
Where Drama Meets Design Welcome to nearly 8,000 square feet of pure fabulous in one of the North Shore’s most prestigious enclaves. This newly reimagined estate has been transformed from top to bottom in the last 24 months, creating a home that is equal parts glamorous, playful, and unforgettable. From the moment you step inside, you’re swept into a world of high style and high impact. The soaring ceilings set the stage, while bold architectural details and designer finishes bring a sense of drama to every room. The custom chef’s kitchen is as functional as it is stunning—perfect for hosting everything from cozy family dinners to glamorous cocktail parties. Every detail was designed to delight. The pink laundry room will make you smile every time you walk in, and the sleek, sophisticated man bar is party-ready for unforgettable nights with friends. Every corner of this home tells a story of creativity, luxury, and fun. Step outside and it only gets better. The grounds are your private resort: a sparkling pool glistening in the sun, a full tennis court for a quick match, and beautifully landscaped gardens that feel like your own private park. Whether you’re entertaining on a grand scale or enjoying quiet evenings under the stars, this property delivers it all.

89 Pound Hollow Road, Old 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.