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$895,000
4 Beds 3 Baths 982950 MLS
Welcome to this spacious 4-bedroom, 2.5-bath two-story home located in the desirable Highpoint Meadows community of Southold. Set on a corner lot, this property offers a welcoming front yard and a generously sized backyard with ample room for a pool and outdoor entertaining. Inside, the home features an open-concept kitchen with new refrigerator, and dining area ideal for everyday living and gatherings, complemented by a formal living room for added versatility. Additional highlights include a convenient laundry room, a two-car attached garage with brand new doors, and a full basement with 8-foot ceilings offering excellent storage and a new hot water heater, gas heat, and potential for future finishing. Perfectly situated to enjoy the North Fork lifestyle, this home is in the Founders Park and Beach Park District, with direct access to a sugar sand beach, park and playground and is just moments from wineries, farm stands, the hamlet, train station, Jitney stop and a variety of shops and restaurants. Easy access to Greenport and Mattituck makes this location both convenient and desirable. A wonderful opportunity to make this home your own and enjoy all that the North Fork has to offer.

240 Lisa Drive, Southold

$999,000
3 Beds 2 Baths 987188 MLS
Welcome to Pine Neck Landing a Private Waterfront Community in East Quogue with Bay Beach & Marina access. This well maintained Ranch home offers 3 Bedrooms 2 Full Bathrooms, Kitchen, Living/Dining Area Combo, Oak Floors Throughout and a 1 Car Garage. From the Dining Area you can enjoy the 3 Season Sunroom which leads to the Rear Deck, perfect for entertaining. The Backyard offers plenty of Privacy that abuts 60+ acres of Nature Conservancy Land. This is a Perfect Waterfront Community Getaway close to everything the Hamptons has to offer and is only a short drive to the Ocean Beaches, Fine Dining, & Shopping. There are endless possibilities with .42 acres of land to upgrade and expand the existing house or build you new dream home.

26 Canvasback Lane, E. Quogue

$2,100,000
4 Beds 4 Baths 973460 MLS
Build your dream home on this exceptional waterfront lot offering unobstructed, forever views and breathtaking sunsets over the pristine waters of the sound. With plans already in place, you can break ground on your custom home without delay. Nestled in one of the most sought-after locations on the North Fork, this property offers the perfect blend of privacy and convenience—just minutes from local vineyards, farm stands, dining, beaches, and marinas. Set in a serene and scenic location, this property offers direct access to miles of beach for peaceful walks along the shore, and is just moments from the tranquil Goldsmith Inlet, perfect for kayaking, paddleboarding, or simply enjoying nature at its finest. Whether you’re looking for a peaceful weekend retreat or a full-time coastal haven, this rare opportunity delivers it all. A one-of-a-kind acre-and-a-half property situated on a 40-foot-high bluff above the Long Island Sound, with clear views of the Connecticut shoreline and gorgeous northwest sunsets! Hidden off North Road (County Road 48) in Peconic, access is via a mile-long private road. This is the final piece of a six-lot subdivision. Delivering a powerful feeling of privacy, in a totally natural setting! Truly a MUST SEE for the individual searching for solitude, privacy, and relaxation! Full Building Permits Approved. Price listed is for vacant lot only including permits to build, which can be modified. Come see this extraordinary location and design your dream home! This listing may include images that have been digitally altered or virtually staged.

4760 Blue Horizon Bluffs, Peconic

$1,995,000
4 Beds 4 Baths 900582 MLS
Two acres of waterfront with beach, ramp and bulkhead.Mediterranean Style home, beautifully situated on Carlls River. Guest Cottage and garden shed with sliders patio and water view. (works for car collector storage too) Gracious home boasting beautiful botanical gardens and landscaping. Designer kitchen and bathrooms, custom cabinetry, and woodwork abounds. Hand painted Turret stairway to Juliet balcony overlooking living room, and 2 additional bedrooms, one with Balcony to Sunset views. Trees and gardens create idyllic setting. Inviting guest cottage with full bath and wrap around decks taking advantage of 203' waterfront with sandy beach. The potting shed can also be repurposed as car storage for the car collector, and kept as is for the avid gardener, boater or fisherman.

50 Cedar Lane, Babylon

$799,000
4 Beds 2 Baths 985781 MLS
Welcome to this spacious four-bedroom, two-bath home nestled in the heart of the Village of Lindenhurst. Set on a large, beautifully sized property, this home offers the perfect blend of comfort, functionality, and outdoor space. Step inside to find a warm and inviting living room featuring a cozy fireplace—ideal for relaxing evenings. The home also boasts a formal dining room perfect for entertaining, along with a well-appointed kitchen ready for everyday living and gatherings alike. With four generously sized bedrooms and two full baths, there’s plenty of room for everyone. Outside, the expansive yard offers endless possibilities for recreation, gardening, or future expansion. A garage adds convenience and additional storage. Don’t miss the opportunity to own this versatile home in a desirable village location close to shops, dining, parks, and transportation.

70 Bristol Street, Lindenhurst

$2,295,000
3 Beds 2 Baths 980008 MLS
Charming 1929 Dutch Colonial-style home ideally situated in the heart of the village, offering convenient access to local amenities including marina, shops, and restaurants. This three- bedroom residence features one full bathroom and one half bathroom, with all bedrooms located on the second floor. The home showcases original architectural details throughout, including classic moldings and solid wood doors, preserving its timeless character. The main level offers a living room with fireplace, a formal dining room, kitchen and half bathroom. Set on a property with both front and backyard space, this home provides room for outdoor enjoyment, entertaining, or future enhancements. Ideal for those seeking a renovation opportunity, investment property or primary residence, this home offers strong potential in desirable village setting. Photo renderings courtesy of AI.

11 Hulse Street, Bellport Village

$2,699,000
6 Beds 6 Baths 980502 MLS
Exquisite Resort-Style Retreat in East Quogue. Recently renovated, turn-key estate set on a sprawling 1.6-acre lot at the end of a private, long driveway, this home offers an unparalleled resort-like setting designed for both grand entertaining and serene relaxation. Spanning 4,100 square feet of meticulously crafted living space, the interior flows seamlessly from one designer room to the next. Chef’s kitchen leads to a bright, inviting breakfast room right next to the formal dining room. Additionally, the first floor offers a large living room with fireplace as well as a private office and den. The second floor offers the large primary bedroom plus junior suite as well as two more bedrooms that share a bathroom, making a total of four bedrooms and three full bathrooms on the second floor. The basement is an additional 2,000 square foot of finished space with plenty of versatility. This level includes two bedrooms with egress windows, a full bathroom, a separate walk-out entrance, a home gym area, and a family room. Located above the detached two-car garage is also a full bonus apartment with kitchen and full bathroom. The expansive backyard has a pristine heated saltwater pool that serves as the centerpiece of the outdoor oasis. There's also basketball with ample room remaining to add a tennis court. True Virtual Tour available upon request.

26 Box Tree Road, E. Quogue

$2,239,000
6 Beds 4 Baths 978923 MLS
Nestled on a full acre in the heart of Shelter Island, this exceptional island retreat offers the perfect blend of relaxed elegance and modern comfort. The main residence features an airy open-concept design ideal for both everyday living and entertaining. A chef’s kitchen anchors the home, seamlessly flowing into the dining and living areas, where a dramatic vaulted ceiling fills the space with natural light and a sense of grandeur. The main home includes four spacious bedrooms and three full baths, offering comfortable accommodations for residents and guests. An attached two-car garage provides convenience, with a versatile bonus room above—perfect for a media room, studio, or additional lounge space. Just across the yard, a charming private cottage offers two bedrooms, a full bath, a living room, and a kitchenette—ideal for guests or a private retreat. Outdoor living is equally inviting. The kitchen opens to a generous deck designed for effortless entertaining, overlooking beautifully landscaped grounds. Enjoy warm summer days by the heated gunite pool, relax around the firepit area, and take in the peaceful surroundings of this southwest-facing property. Across the street, access to West Neck Creek makes kayaking and paddleboarding effortless, offering a true water-lover’s escape. A rare opportunity that captures the essence of coastal living on Shelter Island—where comfort, style, and exceptional indoor-outdoor spaces come together in a truly special setting

14 Freds Lane, Shelter Island

$2,800,000
5 Beds 5 Baths 977439 MLS
Located in the desirable Harborview area of Shelter Island, this modern farmhouse blends luxury, comfort, and coastal living. Just 0.2 miles from a private waterfront association, enjoy easy access to kayaking and the beach. Set on a beautifully landscaped half acre, the home is designed for seamless indoor-outdoor living. The open-concept interior is flooded with natural light, featuring a chef’s kitchen that flows effortlessly to the dining and living areas, highlighting views of the backyard oasis. Outside, relax in the heated pool, outdoor shower, or firepit lounge, or entertain on the spacious deck with retractable awning and covered dining area. With five generous bedrooms, including primary suites on both the first and second floors, the home accommodates guests in style. The upstairs suite features a gas fireplace and covered balcony. The fully finished lower level includes a media room with theater seating, a versatile den or gym with yard access, and a fifth bedroom with a large hall bath. Step inside and start enjoying the best of Shelter Island living.

12 Terry Dr., Shelter Island

$925,000
4 Beds 3 Baths 979588 MLS
Don't miss out on this indescribable treasure! Walk through to experience the superior craftsmanship as well as future potential found in this unique property. Custom built by owner with no expense spared and with only the finest quality materials and finishes. The quality is obvious, starting with the stucco exterior on all sides and authentic New Jersey natural stone throughout the facade which carries through the landscaping. Upon entry, you are greeted to an open floor plan with Brazilian Red Mahoganey wide plank floors, with a custom compass insignia in the entryway, 9-foot ceilings, crown and floor moldings and recessed lighting throughout the main floor. Hamptons style trim around the windows and doors throughout the house. The focal point of the living room is the prominent wood burning fireplace showcasing the same NJ Natural stone as the exterior. The generous primary suite is off the main floor boasting a custom-made fully enclosed steam shower with multiple jets and rain showerhead together with the natural rock shower floor provides for a spa experience. The bathroom is also adorned with a 10-ft tapered ceiling, a jetted tub and two vanities. The Italian porcelain tile radiant heat floor will ensure you never want to leave this oasis. The oversized primary bedroom with an 11-foot ceiling includes 2 separate California style closets. The formal dining room boasts a stunning coffered ceiling and plenty of space for a large dinner party. The eat-in gourmet kitchen is a dream with its beautiful granite counters and Turkish marble mosaic backsplash and spacious Legacy custom cabinetry with pull out cabinet drawers, soft close hardware and glass accent doors. The two-tiered center island allows for food prep while family or guests are spread-out at the seating for 5 at the counter. A beautiful out of the way staircase leads to a fully insulated 1,200 sq ft 2nd floor with 4 dormers and its own electric sub-panel for future use. The 8ft sliding glass doors lead out from the kitchen to a covered patio nook overlooking the 1,100 sq ft bluestone patio with built in fire-pit. The outdoors is tastefully landscaped with specimen trees, bluestone walkways, a concrete half court and perimeter plantings to ensure your own private backyard retreat with plenty of room for an inground pool, outdoor kitchen and more. The lower level hardly feels like a basement with 9-ft ceilings, 6 oversized double hung windows allowing for an abundance of natural light and a private covered entrance. The potential for the lower level's 2,350 sq ft space is limitless. Currently, half the space has 8 ft acoustic drop ceilings, water resistant wood impression flooring, carpeted area, tiled 9x8 full bathroom and separate laundry room with slop sink. The oversized utility room has an industrial size, low septic system with overflow dual pump alarm system for laundry & bathrooms, 200 amp electric panel and an additional sub panel. The commercial grade German Buderus oil burner which is powerful enough to heat the current living space and potential future inground pool, future second floor, future lower floor completion. The other half of the lower level is fully framed & insulated with roughed plumbing and electric (including having its own sub-panel) with the intention of having 2 additional bedrooms, bathroom, kitchen and living space (with proper permits). There are plenty of closets and an extra-thick concrete walled reinforced room. The property is also equipped with a 775 sq ft heated and climate-controlled garage with electric, plumbing and overhead storage space. An abundant amount of space to house whatever fits your fancy. The large back yard shed has ample room for all your gardening and holiday accessories. The house was built with meticulous care and foresight making its appearance as impressive as its structure. This house is a MUST SEE!! You owe it to yourself to schedule a private showing.

16 Oriole Place, Farmingville

$750,000
5 Beds 3 Baths 979189 MLS
Welcome to this spacious and versatile home set on an oversized .44 acre lot just minutes from the Long Island Expressway for easy commuting. This 5 bedroom, 3 full bath home offers the perfect blend of space, comfort, and functionality. Step inside to a bright and airy living room featuring soaring ceilings, exposed beams, and skylights that fill the space with natural light. The home offers an eat-in kitchen with a center island, stainless steel appliances, and ample cabinet space perfect for everyday living and entertaining. A formal dining room provides the ideal setting for gatherings and special occasions. The home features generously sized bedrooms, including multiple large living areas that offer flexibility for extended family, guests, or a home office setup. Updated bathrooms include modern vanities and a beautifully tiled walk-in shower. Additional highlights include central air, forced hot air heating, and a RainSoft water filtration system throughout the entire home. The layout offers a unique and open feel with great natural light in every room. Step outside to your expansive backyard featuring an in-ground pool, patio space, and plenty of room for entertaining, relaxing, or creating your own outdoor oasis. The large driveway and attached garage provide ample parking. This home offers space, character, and convenience all in one. Don’t miss this opportunity to own a unique property with endless potential.

528 Lockwood Drive, Shirley

$699,999
3 Beds 2 Baths 979147 MLS
Step inside this exceptional split-level residence, From the moment you enter, the open and airy living room welcomes you with an abundance of natural light, flowing into the custom kitchen featuring stainless steel appliances, elegant granite countertops and soaring cathedral ceilings. The second floor provides 3 comfortable bedrooms and a full bathroom, The Lower lever offers a versatile space with its own full bathroom and outside entrance that can be used for endless possibilities, weather your envision a cozy family room, a private home office or a comfortable in-law suite with proper permits. The parklike backyard offers you an in-ground pool perfect for entertainment, complementing this remarkable property.

86 Overlook Drive, East Islip

$3,695,000
6 Beds 6 Baths 978627 MLS
Rising along one of the most prestigious stretches of shoreline in Asharoken, this extraordinary waterfront estate represents the largest and most significant residential offerings in the area. Set on approximately 3.43 private, gated acres with an impressive 400 feet of direct sandy beachfront along the Long Island Sound, the property offers exceptional scale, privacy, and uninterrupted water views near Northport Harbor. Encompassing approximately 12,000 square feet, this custom residence is designed for both grand scale entertaining and everyday living. Expansive, light filled interiors feature soaring ceilings, oversized rooms, and walls of glass that capture panoramic waterfront views from nearly every vantage point. Each bedroom is positioned to take full advantage of the coastal setting, offering a private retreat with sweeping water vistas. The home features 6 bedrooms and 6 bathrooms, along with two full kitchens, including a chef’s kitchen with direct outdoor access for seamless indoor outdoor flow. A butler’s kitchen further enhances convenience and entertaining capabilities. Resort style amenities include a saltwater indoor pool, private indoor racquetball court, and a marble spa-style bath. Additional highlights include separate guest quarters and a full length mahogany deck overlooking the harbor, ideal for enjoying sunrise and sunset views. The exterior grounds are equally impressive, featuring custom hardscape with a covered patio, fireplace, and expansive entertaining areas. The property’s 400 feet of private beachfront provides direct water access and a rare sense of seclusion. Modern upgrades include a whole-house generator and a private solar farm. Elevation certificate on file. A rare opportunity to own a premier waterfront estate on Long Island’s North Shore, offering a unique combination of size, setting, and lifestyle with convenient access to Manhattan.

33 Beach Road, Asharoken

$2,375,000
4 Beds 3 Baths 960930 MLS
Rare Waterfront on Shy 4 Acres! Flax Pond Prestige! A waterfront home that shines in every season - 110' of waterfront frontage - One irreplaceable Setting! A rare North-Shore waterfront opportunity, set back from the road and positioned on the most sought-after waterfront views of Flax Pond, Crane Neck and the LI Sound with beach access! After 45 years, the sellers are ready to pass on the title of this once-in-a-lifetime waterfront estate! The home, once a cabin hunting lodge in the 20's was purchased by Mr. Walcott, a Professor of Biology from SUNY Stony Brook in the 60's. A New England native, Mr. Walcott purposely instructed the architect to design a house to appear as an older Saltbox-style home which expanded gradually over many years; hence the multiple roof levels and somewhat irregular layout. While some internal modernization has been undertaken by the present owners, the original character of this house has been respected. Updates include; French drain in basement, filters added to the well, central air conditioning system, inground sprinkler system, Generator, SS kitchen appliances, newer oil burner. The southern meadow, meanwhile, became partially forested and transformed into a scenic lawn, both home to local wildlife, while the northern lawn has reliably served as a front lawn, bird sanctuary, and a thorough and reliable protection against the sea. Bird watch, Kayak, commune with nature and enjoy the harmony of water and wilderness, experiencing the best of both worlds. A home so warm and welcoming. You'll love the sunsets over the water that take your breath away - no matter the season....Where Land, Water, & Legacy Meet!

5 Shore Drive, Setauket

$2,479,000
4 Beds 5 Baths 973930 MLS
Welcome to 675 Pine Tree Rd, a brand-new coastal retreat nestled on a half acre in Cutchogue. Enjoy the rare convenience of dropping your paddle board in creek at the end of the street, strolling around the corner to Broad Cove Marina or heading down the road to Causeway beach just .8 miles away. This beautifully crafted 4-bedroom 5-bathroom luxury residence offers 3,200 s.f. of thoughtfully designed living space flooded with light over size windows and high ceilings, elegant millwork and 3-1/2" white oak flooring throughout. The heart of the home is a stunning chef’s kitchen featuring quartz counter tops, custom cabinetry and Thermador appliances opening to the main living area, perfect for entertaining and enjoying the North Fork lifestyle. The home offers two primary suites, providing exceptional flexibility for owners and guests. A spacious first floor junior suite with cathedral ceiling offers comfort and privacy, while the second-floor primary suite features a tray ceiling, large walk-in shower, soaking tub and his/hers walk in closets. The second floor has a sitting area and two additional en-suite bedrooms with vaulted ceilings and walk in closets. Outdoors, beautiful lush landscaped grounds surround a saltwater heated pool and stone patio, ideal for summer gatherings and entertaining. A rare opportunity to own a brand new home in a premier location with completion expected in July 2026.

675 Pine Tree Road, Cutchogue

$999,000
4 Beds 3 Baths 962515 MLS
PRICE REDUCED!!! SELLERS ARE MOTIVATED! Move-in ready, this Harbor Hills post modern home offers a blend of sophisticated updates and timeless charm. The home has been fully renovated to meet the expectations of modern living. Boasting 4 bedrooms and 3 full baths, the bright, open-concept main floor is filled with natural light throughout, across its contemporary design. The sleek, updated kitchen is a chef’s dream, featuring modern cabinetry, a dedicated wine storage area, and a stylish breakfast bar—perfect for both entertaining and everyday living. On the upper level, the expansive primary suite is a true retreat at over 600 square feet, complete with a double doors, vaulted ceiling, cozy sitting area, custom walk-in closets, and a spa-like ensuite bathroom. You will also find two additional bedrooms and an updated full bath on this level. The lower level offers exceptional flexibility, providing endless possibilities, whether you envision it as a home office, guest quarters, or an inviting family room, and it even includes a full bath and private outside entrance for added convenience. Downstairs, the basement level provides entertaining space with a media room, as well as a storage room with laundry. Set on over half an acre of exquisitely landscaped grounds, the property is a private oasis, complete with a semi in-ground heated pool—ready for this summer's enjoyment. What truly sets this home apart is its location and lifestyle access: Its prime location, within the desirable Port Jefferson School District is near the LIRR, and just a short walk to the beach, golf course, hospitals, and Port Jefferson Village, where you will find the local charm and character of the live theater, parks, shops and restaurants, the convenience of the ferry to New England and even enjoy the marina with waterfront dining and beautiful sunsets over the LI Sound. Residents of the Incorporated Village of Port Jefferson have access to the sought-after north shore lifestyle, with resident-only access to multiple beaches on the Long Island Sound. Port Jefferson is a boater's dream, with several private and public marinas just minutes from Harbor Hills, and easy access to Port Jefferson Harbor offering fishing and water sports. For those considering a move away from the pace of city living, this home offers the opportunity to embrace a more relaxed, coastal lifestyle—without compromising on convenience, connectivity, or quality of life. You'll want to embrace the lifestyle that this North Shore location offers! PLEASE NOTE: With a tax grievance already in progress, the next owner is well-positioned to realize potential annual savings of approximately $2,000–$3,000 for the 2027 tax year. Tax grievance letter attached.

87 Soundview Drive, Port Jefferson

$485,000
3 Beds 2 Baths 973453 MLS
Waterfront Living with Private Dock – Rare Opportunity! Welcome to a unique waterfront property offering the perfect blend of lifestyle, investment potential, and future expansion. Situated on an oversized 0.43-acre lot, this home features direct water access with a private dock—ideal for boating, fishing, kayaking, or simply enjoying peaceful waterfront views right from your backyard. The existing residence offers approximately 1,200+ square feet of living space with 3 bedrooms and 2 full bathrooms. Whether you’re looking to renovate, expand, or rebuild, this property presents endless possibilities to create your dream waterfront home. The expansive lot provides ample space for outdoor entertaining, storage, or future development, making it a standout opportunity for both end-users and investors alike. Located in the desirable Shirley area within the Town of Brookhaven, this home offers convenient access to beaches, marinas, parks, shopping, and major roadways while maintaining a quiet, coastal neighborhood feel. Property Highlights: • Waterfront property with private dock • Oversized 0.43-acre lot • 3 bedrooms / 2 full bathrooms • Approx. 1,284 square feet of living space • Endless renovation, expansion, or rebuild potential • Ideal for boating and outdoor lifestyle • Low taxes. Perfect for: End-users, investors, builders, or anyone seeking a waterfront lifestyle opportunity. Don’t miss this rare chance to own a waterfront property with incredible upside potential in a prime Long Island location.

127 Johns Neck Road, Shirley

$879,000
3 Beds 2 Baths 972288 MLS
Set against a backdrop of preserved farmland, this exquisite move in ready 3-bedroom, 2-bath Mattituck retreat captures the essence of North Fork living with waterviews, farm views and unforgettable, color-drenched sunsets. Designed with an open floor plan, the home is filled with natural light and offers effortless flow for everyday living and entertaining featuring a wood burning fireplace with wood burning cast-iron stove inside. A newly updated kitchen with stainless steel appliances, real wood cabinets and beautifully renovated bathrooms elevate the interior with modern comfort and style. Step outside to an expansive upper deck and lower patio—ideal vantage points to take in the peaceful agricultural landscape and evening skies. Perfectly positioned, enjoy easy access to Love Lane’s beloved boutiques, cafe's, and wineries, while Bailee's Beach is just moments away for sun-soaked days by the water. Located .6 miles from the LIRR and Hampton Jitney. Exceptional living at its finest, this home boasts wood floors and Anderson Windows throughout, brand new AC units, newer boiler, updated septic, new Anderson front door, public water, 2023 new chimney lining and chimney refaced, newer appliances 2019-2024, newer leaf guard gutters and propane for gas cooking. Whether you’re seeking a full-time residence or a weekend escape, this property delivers privacy, proximity, and picturesque beauty in one of the North Fork’s most sought-after locations. This listing may include images that have been digitally altered or virtually staged.

540 Conklin Road, Mattituck

$1,950,000
4 Beds 3 Baths 970247 MLS
Built in 2021 and offered in like-new condition, this stylish four-bedroom residence pairs clean contemporary design with the relaxed ease of North Fork living. A semi-open floor plan creates natural flow across the main level, connecting the living, dining, and kitchen spaces in a layout equally suited for everyday living and effortless entertaining. Four spacious bedrooms offer comfortable accommodations, while a full unfinished basement presents excellent potential for additional living space, whether for a media room, gym, recreation area, or some combination. The primary bedroom enjoys vaulted ceilings, plenty of natural light and a generous ensuite bath. Outside, a heated saltwater pool is set within mature, thoughtfully designed landscaping that provides both privacy and a beautifully established backdrop for summer days. Deeded HOA access to a pristine Sound beach, Eastern Shores, completes this exceptional offering. Located less than a mile from the heart of Greenport Village, home to coveted restaurants, boutique shops, coffee shops, and marinas.

660 Sutton Place, Greenport

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.